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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18) Show 18 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-09-15 17:15:14 UTC

Update Date

2021-09-14 15:43:35 UTC

HMDB ID

HMDB0010332

Secondary Accession Numbers

HMDB10332

Metabolite Identification

Common Name

Bilirubin glucuronide

Description

Bilirubin glucuronide belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). The reaction is a transfer of two glucuronic acid groups including UDP glucuronic acid sequentially to the propionic acid groups of the bilirubin, primarily catalyzed by UGT1A1. Furthermore, those affected may develop kernicterus (deposits of pigment in the brain) that can cause nerve degeneration. Note that biliary duct blockage can also lead to conjugated hyperbilirubinemia but the pathophysiology is that backflow of bilirubin di-glucuronide with little indirect bilirubin and bilirubin glucuronide from bile duct through liver into blood plasma. Normally, there is just a little conjugated bilirubin escapes into the general circulation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241200502D          

 55 59  0  0  1  0            999 V2000
   21.3741   -7.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9450   -9.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3741   -9.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8030   -9.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9450   -7.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8030   -6.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2306   -7.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5175   -7.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0176  -10.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7556   -4.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7813   -9.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1223   -6.9735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4857  -10.3745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9549   -5.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3741   -9.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.6595   -8.7432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0885   -8.7432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.0885   -7.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.6595   -7.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0871   -9.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3334   -8.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1619   -8.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8016   -8.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3773   -7.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0009   -9.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7098   -8.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5161   -9.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1938  -10.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2306   -8.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0424   -7.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8030   -7.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2973   -6.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6139  -10.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8583  -10.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2577   -8.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8124   -6.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0378  -10.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1479   -5.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6253  -11.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7354   -4.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8183  -11.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2874   -4.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7321  -10.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9608  -12.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0411   -4.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9149   -4.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1159   -3.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2052  -12.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5793   -3.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3767  -12.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7098   -9.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9953   -9.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809   -9.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809   -8.4494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664   -9.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
 16  2  1  1  0  0  0
  2 29  1  0  0  0  0
 15  3  1  6  0  0  0
 17  4  1  1  0  0  0
 19  5  1  6  0  0  0
  6 31  1  0  0  0  0
  7 29  2  0  0  0  0
  8 31  2  0  0  0  0
  9 43  2  0  0  0  0
 10 45  2  0  0  0  0
 11 21  1  0  0  0  0
 11 28  1  0  0  0  0
 12 24  1  0  0  0  0
 12 32  1  0  0  0  0
 13 37  1  0  0  0  0
 13 43  1  0  0  0  0
 14 38  1  0  0  0  0
 14 45  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 31  1  6  0  0  0
 20 21  2  0  0  0  0
 20 23  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 27  1  0  0  0  0
 24 26  2  0  0  0  0
 25 28  2  0  0  0  0
 25 33  1  0  0  0  0
 26 30  1  0  0  0  0
 27 29  1  0  0  0  0
 28 34  1  0  0  0  0
 30 32  2  0  0  0  0
 30 35  1  0  0  0  0
 32 36  1  0  0  0  0
 34 37  2  0  0  0  0
 36 38  2  0  0  0  0
 37 39  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
 39 44  1  0  0  0  0
 40 42  2  0  0  0  0
 40 46  1  0  0  0  0
 41 43  1  0  0  0  0
 41 48  1  0  0  0  0
 42 45  1  0  0  0  0
 42 47  1  0  0  0  0
 46 49  2  0  0  0  0
 48 50  2  0  0  0  0
 51 26  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
 55 53  2  0  0  0  0
M  END

HMDB0010332
     RDKit          3D
Bilirubin glucuronide
 99103  0  0  0  0  0  0  0  0999 V2000
    1.6181    9.4516   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912    8.6439   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    7.2177   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349    6.3360   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    6.6021   -2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    4.9830   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    3.8752   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555    2.5882   -0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    2.1790    0.2923 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194    0.9466    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    0.0502    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -0.6177    1.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365   -1.7710    1.1529 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783   -2.0378    1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041   -3.0114    1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437   -3.0861   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6390   -2.2144   -1.0903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640   -2.4930   -2.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5305   -1.9240   -3.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -3.5245   -1.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6015   -4.0187   -2.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941   -3.8702   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9627   -4.8389    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6626   -5.1736    1.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8753   -0.9633    2.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2170   -0.8419    3.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.0821    2.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906    1.2667    3.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    2.0642    2.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081    2.1192    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463    3.2463    0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855    1.0640    0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6626    0.5441   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359   -0.7743   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -0.5001    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4868   -1.6734    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9030   -2.6106    1.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277   -1.8699    0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4821   -3.0535    0.7243 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7361   -2.7790    1.4918 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8114   -3.3338    2.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9684   -3.1389    0.6367 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0223   -2.4077    1.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6113   -2.6771   -0.7614 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7654   -2.5682   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736   -1.9058   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7815   -3.1931   -2.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6464   -3.4695   -1.3551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -3.9430   -0.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0004   -5.2571   -0.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    1.5420   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    1.5768   -2.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683    5.1270   -0.1700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    6.5072   -0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    7.0303    0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    9.2089   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   10.5221   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0786    9.0336   -2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    6.3217   -2.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    5.9561   -3.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    7.6668   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105    3.9230   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0917    2.8030    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    0.6120    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.8101    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.4120    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -3.6871    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409   -1.5389   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1260   -4.3626   -3.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3072   -3.2070   -2.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1868   -4.8217   -2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8610   -5.2348   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7359   -6.0575    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4270   -5.4407    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -0.3796    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0569   -0.2959    3.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5117   -1.8906    3.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.1232    4.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    1.7584    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    3.1526    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154    1.6980    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923    0.8348   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643   -0.9580   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -1.5965   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.0258    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    0.2675   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -3.6339    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -1.6482    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810   -3.9500    2.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251   -4.2281    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -2.9316    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1130   -1.6627   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0018   -2.9528   -3.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.9863   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2230   -5.7869    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.9787   -2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430    2.6374   -2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.2237   -3.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    4.3883    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
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 53 99  1  0
M  END


  Mrv0541 02241200502D          

 55 59  0  0  1  0            999 V2000
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  1 18  1  0  0  0  0
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 16  2  1  1  0  0  0
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 38 40  1  0  0  0  0
 39 41  2  0  0  0  0
 39 44  1  0  0  0  0
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 46 49  2  0  0  0  0
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 51 26  1  0  0  0  0
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 55 53  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010332

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

> <INCHI_IDENTIFIER>
InChI=1S/C39H44N4O12/c1-7-20-19(6)36(49)43-27(20)14-25-17(4)22(9-11-30(44)45)28(41-25)15-29-23(18(5)24(40-29)13-26-16(3)21(8-2)37(50)42-26)10-12-31(46)54-35-33(48)32(47)34(38(51)52)55-39(35)53/h7-8,13-14,32-35,39-41,47-48,53H,1-2,9-12,15H2,3-6H3,(H,42,50)(H,43,49)(H,44,45)(H,51,52)/b26-13-,27-14-/t32-,33-,34-,35+,39+/m0/s1

> <INCHI_KEY>
NCZCFMOVDHRJII-VBORGTJOSA-N

> <FORMULA>
C39H44N4O12

> <MOLECULAR_WEIGHT>
760.7863

> <EXACT_MASS>
760.295572892

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
81.72297107874331

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
1.1713128976666671

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.37573133920223

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2065422059986433

> <JCHEM_PKA_STRONGEST_BASIC>
-3.701179343887323

> <JCHEM_POLAR_SURFACE_AREA>
260.59999999999997

> <JCHEM_REFRACTIVITY>
201.19460000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010332
     RDKit          3D
Bilirubin glucuronide
 99103  0  0  0  0  0  0  0  0999 V2000
    1.6181    9.4516   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.3072   -3.2070   -2.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1868   -4.8217   -2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8610   -5.2348   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7359   -6.0575    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4270   -5.4407    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -0.3796    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0569   -0.2959    3.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5117   -1.8906    3.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.1232    4.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    1.7584    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    3.1526    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154    1.6980    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923    0.8348   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643   -0.9580   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -1.5965   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.0258    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    0.2675   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -3.6339    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -1.6482    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810   -3.9500    2.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251   -4.2281    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -2.9316    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1130   -1.6627   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0018   -2.9528   -3.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.9863   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2230   -5.7869    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.9787   -2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430    2.6374   -2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.2237   -3.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    4.3883    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 45 46  2  0
 45 47  1  0
 44 48  1  0
 48 49  1  0
 49 50  1  0
 33 51  1  0
 51 52  1  0
  6 53  1  0
 53 54  1  0
 54 55  2  0
 54  3  1  0
 51  8  2  0
 27 12  2  0
 49 39  1  0
 22 16  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  5 59  1  0
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  5 61  1  0
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  9 63  1  0
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 32 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 39 87  1  1
 40 88  1  1
 41 89  1  0
 42 90  1  6
 43 91  1  0
 44 92  1  1
 47 93  1  0
 49 94  1  6
 50 95  1  0
 52 96  1  0
 52 97  1  0
 52 98  1  0
 53 99  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      39.898 -14.011   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.231 -17.091   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      39.898 -18.631   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      42.566 -17.091   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      37.231 -14.011   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      42.566 -12.471   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      35.897 -14.781   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      43.899 -14.781   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.300 -19.222   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      29.410  -7.743   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      29.458 -17.609   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      28.228 -13.017   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      27.040 -19.366   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      27.916 -10.044   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      39.898 -17.091   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.564 -16.321   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.232 -16.321   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.232 -14.781   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.564 -14.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.896 -17.091   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.489 -16.464   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.169 -14.958   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.230 -16.321   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.704 -14.482   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.735 -18.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.458 -15.387   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      34.563 -17.091   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.228 -18.942   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      35.897 -16.321   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.212 -14.482   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      42.566 -14.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.688 -13.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      32.879 -19.653   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.602 -20.349   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.748 -14.958   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      25.783 -11.771   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      28.071 -20.510   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      26.409 -10.364   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      27.301 -21.844   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.639  -9.031   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      25.794 -21.524   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      26.670  -7.886   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.633 -19.992   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.927 -23.251   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      28.077  -8.513   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      24.108  -8.870   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.350  -6.380   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      24.650 -22.554   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.481  -7.463   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      24.970 -24.061   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      27.458 -16.927   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.125 -17.697   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      24.791 -16.927   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      24.791 -15.772   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      23.457 -17.697   0.000  0.00  0.00           O+0
CONECT    1   18   19                                                       
CONECT    2   16   29                                                       
CONECT    3   15                                                            
CONECT    4   17                                                            
CONECT    5   19                                                            
CONECT    6   31                                                            
CONECT    7   29                                                            
CONECT    8   31                                                            
CONECT    9   43                                                            
CONECT   10   45                                                            
CONECT   11   21   28                                                       
CONECT   12   24   32                                                       
CONECT   13   37   43                                                       
CONECT   14   38   45                                                       
CONECT   15    3   16   17                                                  
CONECT   16    2   15   19                                                  
CONECT   17    4   15   18                                                  
CONECT   18    1   17   31                                                  
CONECT   19    1    5   16                                                  
CONECT   20   21   23   25                                                  
CONECT   21   11   20   22                                                  
CONECT   22   21   24                                                       
CONECT   23   20   27                                                       
CONECT   24   12   22   26                                                  
CONECT   25   20   28   33                                                  
CONECT   26   24   30   51                                                  
CONECT   27   23   29                                                       
CONECT   28   11   25   34                                                  
CONECT   29    2    7   27                                                  
CONECT   30   26   32   35                                                  
CONECT   31    6    8   18                                                  
CONECT   32   12   30   36                                                  
CONECT   33   25                                                            
CONECT   34   28   37                                                       
CONECT   35   30                                                            
CONECT   36   32   38                                                       
CONECT   37   13   34   39                                                  
CONECT   38   14   36   40                                                  
CONECT   39   37   41   44                                                  
CONECT   40   38   42   46                                                  
CONECT   41   39   43   48                                                  
CONECT   42   40   45   47                                                  
CONECT   43    9   13   41                                                  
CONECT   44   39                                                            
CONECT   45   10   14   42                                                  
CONECT   46   40   49                                                       
CONECT   47   42                                                            
CONECT   48   41   50                                                       
CONECT   49   46                                                            
CONECT   50   48                                                            
CONECT   51   26   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

COMPND    HMDB0010332
HETATM    1  C1  UNL     1       1.618   9.452  -0.774  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.791   8.644  -1.360  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.779   7.218  -1.073  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.035   6.336  -1.643  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.082   6.602  -2.667  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.215   4.983  -1.122  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.359   3.875  -1.497  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.055   2.588  -0.907  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.516   2.179   0.292  1.00  0.00           N  
HETATM   10  C9  UNL     1      -0.119   0.947   0.569  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.462   0.050   1.651  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.780  -0.618   1.684  1.00  0.00           C  
HETATM   13  N2  UNL     1      -2.237  -1.771   1.153  1.00  0.00           N  
HETATM   14  C12 UNL     1      -3.478  -2.038   1.503  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.504  -3.011   1.171  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.044  -3.086  -0.032  1.00  0.00           C  
HETATM   17  N3  UNL     1      -4.639  -2.214  -1.090  1.00  0.00           N  
HETATM   18  C15 UNL     1      -5.564  -2.493  -2.164  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.531  -1.924  -3.262  1.00  0.00           O  
HETATM   20  C16 UNL     1      -6.497  -3.524  -1.714  1.00  0.00           C  
HETATM   21  C17 UNL     1      -7.601  -4.019  -2.582  1.00  0.00           C  
HETATM   22  C18 UNL     1      -6.194  -3.870  -0.477  1.00  0.00           C  
HETATM   23  C19 UNL     1      -6.963  -4.839   0.334  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.663  -5.174   1.500  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.875  -0.963   2.338  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.217  -0.842   3.009  1.00  0.00           C  
HETATM   27  C23 UNL     1      -2.838  -0.082   2.448  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.891   1.267   3.077  1.00  0.00           C  
HETATM   29  C25 UNL     1      -3.899   2.064   2.271  1.00  0.00           C  
HETATM   30  C26 UNL     1      -3.708   2.119   0.845  1.00  0.00           C  
HETATM   31  O2  UNL     1      -3.846   3.246   0.259  1.00  0.00           O  
HETATM   32  O3  UNL     1      -3.385   1.064   0.006  1.00  0.00           O  
HETATM   33  C27 UNL     1       0.663   0.544  -0.529  1.00  0.00           C  
HETATM   34  C28 UNL     1       1.436  -0.774  -0.524  1.00  0.00           C  
HETATM   35  C29 UNL     1       2.680  -0.500   0.340  1.00  0.00           C  
HETATM   36  C30 UNL     1       3.487  -1.673   0.648  1.00  0.00           C  
HETATM   37  O4  UNL     1       2.903  -2.611   1.298  1.00  0.00           O  
HETATM   38  O5  UNL     1       4.828  -1.870   0.315  1.00  0.00           O  
HETATM   39  C31 UNL     1       5.482  -3.053   0.724  1.00  0.00           C  
HETATM   40  C32 UNL     1       6.736  -2.779   1.492  1.00  0.00           C  
HETATM   41  O6  UNL     1       6.811  -3.334   2.733  1.00  0.00           O  
HETATM   42  C33 UNL     1       7.968  -3.139   0.637  1.00  0.00           C  
HETATM   43  O7  UNL     1       9.022  -2.408   1.105  1.00  0.00           O  
HETATM   44  C34 UNL     1       7.611  -2.677  -0.761  1.00  0.00           C  
HETATM   45  C35 UNL     1       8.765  -2.568  -1.663  1.00  0.00           C  
HETATM   46  O8  UNL     1       9.774  -1.906  -1.331  1.00  0.00           O  
HETATM   47  O9  UNL     1       8.781  -3.193  -2.907  1.00  0.00           O  
HETATM   48  O10 UNL     1       6.646  -3.469  -1.355  1.00  0.00           O  
HETATM   49  C36 UNL     1       5.701  -3.943  -0.480  1.00  0.00           C  
HETATM   50  O11 UNL     1       6.000  -5.257  -0.107  1.00  0.00           O  
HETATM   51  C37 UNL     1       0.694   1.542  -1.418  1.00  0.00           C  
HETATM   52  C38 UNL     1       1.415   1.577  -2.711  1.00  0.00           C  
HETATM   53  N4  UNL     1       1.268   5.127  -0.170  1.00  0.00           N  
HETATM   54  C39 UNL     1       1.621   6.507  -0.135  1.00  0.00           C  
HETATM   55  O12 UNL     1       2.522   7.030   0.593  1.00  0.00           O  
HETATM   56  H1  UNL     1       2.357   9.209  -0.042  1.00  0.00           H  
HETATM   57  H2  UNL     1       1.587  10.522  -1.032  1.00  0.00           H  
HETATM   58  H3  UNL     1       0.079   9.034  -2.092  1.00  0.00           H  
HETATM   59  H4  UNL     1      -2.075   6.322  -2.202  1.00  0.00           H  
HETATM   60  H5  UNL     1      -0.878   5.956  -3.535  1.00  0.00           H  
HETATM   61  H6  UNL     1      -1.098   7.667  -2.986  1.00  0.00           H  
HETATM   62  H7  UNL     1      -1.111   3.923  -2.292  1.00  0.00           H  
HETATM   63  H8  UNL     1      -1.092   2.803   0.905  1.00  0.00           H  
HETATM   64  H9  UNL     1      -0.281   0.612   2.603  1.00  0.00           H  
HETATM   65  H10 UNL     1       0.280  -0.810   1.739  1.00  0.00           H  
HETATM   66  H11 UNL     1      -1.678  -2.412   0.527  1.00  0.00           H  
HETATM   67  H12 UNL     1      -4.838  -3.687   1.926  1.00  0.00           H  
HETATM   68  H13 UNL     1      -3.841  -1.539  -1.062  1.00  0.00           H  
HETATM   69  H14 UNL     1      -7.126  -4.363  -3.542  1.00  0.00           H  
HETATM   70  H15 UNL     1      -8.307  -3.207  -2.864  1.00  0.00           H  
HETATM   71  H16 UNL     1      -8.187  -4.822  -2.133  1.00  0.00           H  
HETATM   72  H17 UNL     1      -7.861  -5.235  -0.190  1.00  0.00           H  
HETATM   73  H18 UNL     1      -7.736  -6.057   1.664  1.00  0.00           H  
HETATM   74  H19 UNL     1      -6.427  -5.441   2.424  1.00  0.00           H  
HETATM   75  H20 UNL     1      -5.982  -0.380   2.374  1.00  0.00           H  
HETATM   76  H21 UNL     1      -5.057  -0.296   3.956  1.00  0.00           H  
HETATM   77  H22 UNL     1      -5.512  -1.891   3.304  1.00  0.00           H  
HETATM   78  H23 UNL     1      -3.264   1.123   4.117  1.00  0.00           H  
HETATM   79  H24 UNL     1      -1.890   1.758   3.058  1.00  0.00           H  
HETATM   80  H25 UNL     1      -3.888   3.153   2.657  1.00  0.00           H  
HETATM   81  H26 UNL     1      -4.915   1.698   2.510  1.00  0.00           H  
HETATM   82  H27 UNL     1      -3.992   0.835  -0.780  1.00  0.00           H  
HETATM   83  H28 UNL     1       1.764  -0.958  -1.533  1.00  0.00           H  
HETATM   84  H29 UNL     1       0.824  -1.597  -0.162  1.00  0.00           H  
HETATM   85  H30 UNL     1       2.355   0.026   1.244  1.00  0.00           H  
HETATM   86  H31 UNL     1       3.313   0.268  -0.240  1.00  0.00           H  
HETATM   87  H32 UNL     1       4.773  -3.634   1.359  1.00  0.00           H  
HETATM   88  H33 UNL     1       6.827  -1.648   1.611  1.00  0.00           H  
HETATM   89  H34 UNL     1       6.081  -3.950   2.918  1.00  0.00           H  
HETATM   90  H35 UNL     1       8.125  -4.228   0.728  1.00  0.00           H  
HETATM   91  H36 UNL     1       9.891  -2.932   1.183  1.00  0.00           H  
HETATM   92  H37 UNL     1       7.113  -1.663  -0.621  1.00  0.00           H  
HETATM   93  H38 UNL     1       8.002  -2.953  -3.513  1.00  0.00           H  
HETATM   94  H39 UNL     1       4.738  -3.986  -1.018  1.00  0.00           H  
HETATM   95  H40 UNL     1       5.223  -5.787   0.169  1.00  0.00           H  
HETATM   96  H41 UNL     1       2.352   0.979  -2.648  1.00  0.00           H  
HETATM   97  H42 UNL     1       1.643   2.637  -2.913  1.00  0.00           H  
HETATM   98  H43 UNL     1       0.758   1.224  -3.525  1.00  0.00           H  
HETATM   99  H44 UNL     1       1.715   4.388   0.408  1.00  0.00           H  
CONECT    1    2    2   56   57
CONECT    2    3   58
CONECT    3    4    4   54
CONECT    4    5    6
CONECT    5   59   60   61
CONECT    6    7    7   53
CONECT    7    8   62
CONECT    8    9   51   51
CONECT    9   10   63
CONECT   10   11   33   33
CONECT   11   12   64   65
CONECT   12   13   27   27
CONECT   13   14   66
CONECT   14   15   25   25
CONECT   15   16   16   67
CONECT   16   17   22
CONECT   17   18   68
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   69   70   71
CONECT   22   23
CONECT   23   24   24   72
CONECT   24   73   74
CONECT   25   26   27
CONECT   26   75   76   77
CONECT   27   28
CONECT   28   29   78   79
CONECT   29   30   80   81
CONECT   30   31   31   32
CONECT   32   82
CONECT   33   34   51
CONECT   34   35   83   84
CONECT   35   36   85   86
CONECT   36   37   37   38
CONECT   38   39
CONECT   39   40   49   87
CONECT   40   41   42   88
CONECT   41   89
CONECT   42   43   44   90
CONECT   43   91
CONECT   44   45   48   92
CONECT   45   46   46   47
CONECT   47   93
CONECT   48   49
CONECT   49   50   94
CONECT   50   95
CONECT   51   52
CONECT   52   96   97   98
CONECT   53   54   99
CONECT   54   55   55
END

HMDB0010332
     RDKit          3D
Bilirubin glucuronide
 99103  0  0  0  0  0  0  0  0999 V2000
    1.6181    9.4516   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7912    8.6439   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    7.2177   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349    6.3360   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    6.6021   -2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152    4.9830   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    3.8752   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555    2.5882   -0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    2.1790    0.2923 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194    0.9466    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    0.0502    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -0.6177    1.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365   -1.7710    1.1529 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783   -2.0378    1.5026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5041   -3.0114    1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437   -3.0861   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6390   -2.2144   -1.0903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5640   -2.4930   -2.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5305   -1.9240   -3.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -3.5245   -1.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6015   -4.0187   -2.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941   -3.8702   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9627   -4.8389    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6626   -5.1736    1.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8753   -0.9633    2.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2170   -0.8419    3.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.0821    2.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906    1.2667    3.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    2.0642    2.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081    2.1192    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463    3.2463    0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3855    1.0640    0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6626    0.5441   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359   -0.7743   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802   -0.5001    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4868   -1.6734    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9030   -2.6106    1.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277   -1.8699    0.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4821   -3.0535    0.7243 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7361   -2.7790    1.4918 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8114   -3.3338    2.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9684   -3.1389    0.6367 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0223   -2.4077    1.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6113   -2.6771   -0.7614 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7654   -2.5682   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736   -1.9058   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7815   -3.1931   -2.9071 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6464   -3.4695   -1.3551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -3.9430   -0.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0004   -5.2571   -0.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    1.5420   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    1.5768   -2.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683    5.1270   -0.1700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    6.5072   -0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    7.0303    0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    9.2089   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   10.5221   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0786    9.0336   -2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    6.3217   -2.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    5.9561   -3.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    7.6668   -2.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105    3.9230   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0917    2.8030    0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    0.6120    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.8101    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.4120    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -3.6871    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409   -1.5389   -1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1260   -4.3626   -3.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3072   -3.2070   -2.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1868   -4.8217   -2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8610   -5.2348   -0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7359   -6.0575    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4270   -5.4407    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9822   -0.3796    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0569   -0.2959    3.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5117   -1.8906    3.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.1232    4.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    1.7584    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    3.1526    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154    1.6980    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9923    0.8348   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643   -0.9580   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -1.5965   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.0258    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135    0.2675   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -3.6339    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -1.6482    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0810   -3.9500    2.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1251   -4.2281    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -2.9316    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1130   -1.6627   -0.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0018   -2.9528   -3.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -3.9863   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2230   -5.7869    0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.9787   -2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430    2.6374   -2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.2237   -3.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    4.3883    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 45 46  2  0
 45 47  1  0
 44 48  1  0
 48 49  1  0
 49 50  1  0
 33 51  1  0
 51 52  1  0
  6 53  1  0
 53 54  1  0
 54 55  2  0
 54  3  1  0
 51  8  2  0
 27 12  2  0
 49 39  1  0
 22 16  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  5 59  1  0
  5 60  1  0
  5 61  1  0
  7 62  1  0
  9 63  1  0
 11 64  1  0
 11 65  1  0
 13 66  1  0
 15 67  1  0
 17 68  1  0
 21 69  1  0
 21 70  1  0
 21 71  1  0
 23 72  1  0
 24 73  1  0
 24 74  1  0
 26 75  1  0
 26 76  1  0
 26 77  1  0
 28 78  1  0
 28 79  1  0
 29 80  1  0
 29 81  1  0
 32 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  0
 35 86  1  0
 39 87  1  1
 40 88  1  1
 41 89  1  0
 42 90  1  6
 43 91  1  0
 44 92  1  1
 47 93  1  0
 49 94  1  6
 50 95  1  0
 52 96  1  0
 52 97  1  0
 52 98  1  0
 53 99  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	HMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	HMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid mono-beta-D-glucopyranuronosyl ester	HMDB
2,17-Diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid mono-beta-delta-glucopyranuronosyl ester	HMDB
Bilirubin glucuronate	HMDB
Bilirubin glucuronic acid conjugates	HMDB
Bilirubin monoglucuronide	HMDB
Glucuronic acid conjugates OF bilirubin	HMDB
mono-beta-delta-Glucopyranuronosyl ester 2,17-diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	HMDB
mono-beta-delta-Glucopyranuronosyl ester 2,17-diethenyl-1,10-19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	HMDB
(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylate	HMDB
Glucuronate conjugates OF bilirubin	HMDB

Chemical Formula

C₃₉H₄₄N₄O₁₂

Average Molecular Weight

760.7863

Monoisotopic Molecular Weight

760.295572892

IUPAC Name

(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,6-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

InChI Identifier

InChI=1S/C39H44N4O12/c1-7-20-19(6)36(49)43-27(20)14-25-17(4)22(9-11-30(44)45)28(41-25)15-29-23(18(5)24(40-29)13-26-16(3)21(8-2)37(50)42-26)10-12-31(46)54-35-33(48)32(47)34(38(51)52)55-39(35)53/h7-8,13-14,32-35,39-41,47-48,53H,1-2,9-12,15H2,3-6H3,(H,42,50)(H,43,49)(H,44,45)(H,51,52)/b26-13-,27-14-/t32-,33-,34-,35+,39+/m0/s1

InChI Key

NCZCFMOVDHRJII-VBORGTJOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Glucuronic acid or derivatives
Hexose monosaccharide
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Monosaccharide
Hydroxy acid
Oxane
Fatty acyl
Substituted pyrrole
Pyran
Heteroaromatic compound
Pyrrole
Pyrroline
Secondary carboxylic acid amide
Hemiacetal
Lactam
Carboxylic acid ester
1,2-diol
Carboxamide group
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010332)

Organ

Liver (HMDB: HMDB0010332)
Kidney (HMDB: HMDB0010332)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010332)

Source

Endogenous

Endogenous (HMDB: HMDB0010332)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.51	ALOGPS
logP	1.17	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	260.6 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	201.19 m³·mol⁻¹	ChemAxon
Polarizability	81.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	270.405	30932474
DeepCCS	[M-H]-	268.662	30932474
DeepCCS	[M-2H]-	302.695	30932474
DeepCCS	[M+Na]+	276.65	30932474
AllCCS	[M+H]+	268.0	32859911
AllCCS	[M+H-H2O]+	267.4	32859911
AllCCS	[M+NH4]+	268.7	32859911
AllCCS	[M+Na]+	268.8	32859911
AllCCS	[M-H]-	269.9	32859911
AllCCS	[M+Na-2H]-	274.9	32859911
AllCCS	[M+HCOO]-	280.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.66 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4321 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3393.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	157.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	151.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	545.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	736.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1396.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	736.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2199.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	483.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	223.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	114.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bilirubin glucuronide	CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1	8459.9	Standard polar	33892256
Bilirubin glucuronide	CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1	3870.6	Standard non polar	33892256
Bilirubin glucuronide	CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(=O)O[C@H]3[C@H](O)O[C@@H]([C@@H](O)[C@@H]3O)C(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1	7102.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilirubin glucuronide GC-MS (TBDMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Positive-QTOF	splash10-002f-0300030900-0865b86b083bbe063f3b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Positive-QTOF	splash10-00os-0900150700-a3d05b0eb0cb1285c343	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Positive-QTOF	splash10-004j-3900134200-ca8293fb4addf5c11e9e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Negative-QTOF	splash10-067l-2400044900-10373cf294707957940e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Negative-QTOF	splash10-00lu-4700091400-55082bd1b554e6e72fad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Negative-QTOF	splash10-05o0-6300090000-9b0c34749943f4dd7f98	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Negative-QTOF	splash10-057i-9100077600-20e650c74f102f68001c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Negative-QTOF	splash10-053l-7300097300-9da993c164d046106b50	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Negative-QTOF	splash10-000l-5090671000-d3c50eb55fd5219cae71	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 10V, Positive-QTOF	splash10-01ox-0010120900-f4caa7fa954314bd2ce3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 20V, Positive-QTOF	splash10-02tc-0010332900-c5e0d05638e77b1c92c0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilirubin glucuronide 40V, Positive-QTOF	splash10-0v0r-0895346200-dcb90c3f6d2d07f63a12	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027484

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Bilirubin glucuronide

METLIN ID

Not Available

PubChem Compound

6438344

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

References

Meunier CJ, Verbeeck RK: Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug Metab Dispos. 1999 Jan;27(1):26-31. [PubMed:9884306 ]

Enzyme Details

4. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Enzyme Details

5. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Enzyme Details

6. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Enzyme Details

7. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Meunier CJ, Verbeeck RK: Glucuronidation of R- and S-ketoprofen, acetaminophen, and diflunisal by liver microsomes of adjuvant-induced arthritic rats. Drug Metab Dispos. 1999 Jan;27(1):26-31. [PubMed:9884306 ]

Enzyme Details

8. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Enzyme Details

9. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

Enzyme Details

10. UDP-glucuronosyltransferase 2B17

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:: UGT2B17
Uniprot ID:: O75795
Molecular weight:: 61094.915

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for Bilirubin glucuronide (HMDB0010332)

MOL for HMDB0010332 (Bilirubin glucuronide)

3D MOL for HMDB0010332 (Bilirubin glucuronide)

3D SDF for HMDB0010332 (Bilirubin glucuronide)

3D-SDF for HMDB0010332 (Bilirubin glucuronide)

PDB for HMDB0010332 (Bilirubin glucuronide)

3D PDB for HMDB0010332 (Bilirubin glucuronide)

SMILES for HMDB0010332 (Bilirubin glucuronide)

INCHI for HMDB0010332 (Bilirubin glucuronide)

Structure for HMDB0010332 (Bilirubin glucuronide)

3D Structure for HMDB0010332 (Bilirubin glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References