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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 19:40:38 UTC

Update Date

2021-09-14 15:41:25 UTC

HMDB ID

HMDB0004483

Secondary Accession Numbers

HMDB04483

Metabolite Identification

Common Name

Estrone glucuronide

Description

Estrone-glucuronide is the dominant metabolite of estradiol. Estrone glucuronide is formed by a UDP glucuronyltransferase (EC 2.4.1.17, UTP) reaction creating a much more water-soluble form of the hormone; glucuronides are the most abundant estrogen conjugates. Measurement of estrone-glucuronide is used as one reference method for determining ovulation (immunotubes are available for measuring urinary estrone glucuronide in conjunction with LH, one of the most advanced of ovulation prediction products). (PMID: 14742773 , 1755456 ).

Structure

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

HMDB04483.mol
  Mrv0541 02231219562D          

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M  END

HMDB0004483
     RDKit          3D
Estrone glucuronide
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M  END

HMDB04483.mol
  Mrv0541 02231219562D          

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M  END
> <DATABASE_ID>
HMDB0004483

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1

> <INCHI_KEY>
FJAZVHYPASAQKM-JBAURARKSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.4902

> <EXACT_MASS>
446.194067936

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
46.77478379122559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.361235478666667

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216821222809472

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.300315342672925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267622517834

> <JCHEM_POLAR_SURFACE_AREA>
133.51999999999998

> <JCHEM_REFRACTIVITY>
111.09419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estrone-3-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004483
     RDKit          3D
Estrone glucuronide
 62 66  0  0  0  0  0  0  0  0999 V2000
    4.6558    1.3418   -1.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.2766   -0.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7266   -1.1009   -1.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2431   -1.2212   -1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5272   -0.7893    0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0797   -0.6963   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3881   -1.0404   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -0.9110   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378   -0.4346   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893   -0.3188   -0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108    0.1282    0.6970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9045   -0.8524    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225   -1.1306    0.2426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5228   -2.0307   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602   -2.4899   -1.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4520   -2.4060   -1.8406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7010    0.0692   -0.2441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4678    0.5572    0.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7903    1.1454   -0.7539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2883    0.8759   -2.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046    1.3987    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2207    2.0702    1.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0939    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397   -0.2249    1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    0.1380    2.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.9582    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    0.5875    0.5953 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4705    0.4805    0.8066 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1641    1.6980    1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868    1.5698    0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5171    0.4831   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4518   -0.0969   -0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    2.3185   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401    1.4041   -2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    1.1620   -2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1685   -1.2749   -2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -1.8304   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.7230   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -2.3115   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -1.4918    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -1.4092   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154   -1.1795   -2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    0.4093    1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6724   -1.7399    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5423   -1.7821   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3531   -0.2704   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4043    0.2562    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3874    2.0775   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0167    1.0485   -2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9367    2.0391   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561    2.5343    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    0.2884    1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129   -0.8435    2.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250    0.6583    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    2.0320    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    0.9396    2.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    1.3538   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7100   -0.4369    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.6177    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666    1.6187    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7746    2.5167    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3252    1.4023    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 28  2  1  0
 31  2  1  0
 27  5  1  0
 24  6  1  0
 21 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  1
  7 41  1  0
  8 42  1  0
 11 43  1  1
 13 44  1  1
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  6
 20 49  1  0
 21 50  1  6
 22 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  6
 28 58  1  1
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04483.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.185  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.185  -1.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.149  -2.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.483  -1.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.483  -0.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.149   0.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.816  -2.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.150  -1.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.150  -0.200   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816   0.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.484   0.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.484   2.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.150   2.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.816   2.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.948   0.094   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.853   1.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.948   2.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.520  -0.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.520  -1.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.186  -2.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.852  -1.740   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.852  -0.201   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.186   0.570   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.186   2.110   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.519  -2.510   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.853  -2.510   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.853   0.570   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.186  -4.050   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       1.483   1.340   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.484  -0.970   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.150   1.340   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0       7.424   4.050   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.644   3.641   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.852   2.880   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.520   2.880   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9    5   14   29                                             
CONECT   11    9   12   15   30                                             
CONECT   12   11   13   17   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   32                                                  
CONECT   18   19   23   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   34   35                                                  
CONECT   25   21    2                                                       
CONECT   26   19                                                            
CONECT   27   18                                                            
CONECT   28   20                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31    9                                                            
CONECT   32   17                                                            
CONECT   33   12                                                            
CONECT   34   24                                                            
CONECT   35   24                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0004483
HETATM    1  C1  UNL     1       4.656   1.342  -1.549  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.100   0.277  -0.579  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.727  -1.101  -1.016  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.243  -1.221  -1.121  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.527  -0.789   0.111  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.080  -0.696  -0.057  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.388  -1.040  -1.195  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.976  -0.911  -1.242  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.738  -0.435  -0.169  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.089  -0.319  -0.249  1.00  0.00           O  
HETATM   11  C10 UNL     1      -4.011   0.128   0.697  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.904  -0.852   1.100  1.00  0.00           O  
HETATM   13  C11 UNL     1      -5.923  -1.131   0.243  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.523  -2.031  -0.879  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.360  -2.490  -1.020  1.00  0.00           O  
HETATM   16  O4  UNL     1      -6.452  -2.406  -1.841  1.00  0.00           O  
HETATM   17  C13 UNL     1      -6.701   0.069  -0.244  1.00  0.00           C  
HETATM   18  O5  UNL     1      -7.468   0.557   0.816  1.00  0.00           O  
HETATM   19  C14 UNL     1      -5.790   1.145  -0.754  1.00  0.00           C  
HETATM   20  O6  UNL     1      -5.288   0.876  -2.018  1.00  0.00           O  
HETATM   21  C15 UNL     1      -4.705   1.399   0.257  1.00  0.00           C  
HETATM   22  O7  UNL     1      -5.221   2.070   1.362  1.00  0.00           O  
HETATM   23  C16 UNL     1      -1.035  -0.094   0.963  1.00  0.00           C  
HETATM   24  C17 UNL     1       0.340  -0.225   1.009  1.00  0.00           C  
HETATM   25  C18 UNL     1       1.132   0.138   2.231  1.00  0.00           C  
HETATM   26  C19 UNL     1       2.325   0.958   1.869  1.00  0.00           C  
HETATM   27  C20 UNL     1       3.002   0.588   0.595  1.00  0.00           C  
HETATM   28  C21 UNL     1       4.470   0.480   0.807  1.00  0.00           C  
HETATM   29  C22 UNL     1       5.164   1.698   1.288  1.00  0.00           C  
HETATM   30  C23 UNL     1       6.587   1.570   0.727  1.00  0.00           C  
HETATM   31  C24 UNL     1       6.517   0.483  -0.283  1.00  0.00           C  
HETATM   32  O8  UNL     1       7.452  -0.097  -0.750  1.00  0.00           O  
HETATM   33  H1  UNL     1       4.619   2.318  -1.031  1.00  0.00           H  
HETATM   34  H2  UNL     1       5.440   1.404  -2.335  1.00  0.00           H  
HETATM   35  H3  UNL     1       3.686   1.162  -2.008  1.00  0.00           H  
HETATM   36  H4  UNL     1       5.169  -1.275  -2.022  1.00  0.00           H  
HETATM   37  H5  UNL     1       5.195  -1.830  -0.336  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.910  -0.723  -2.042  1.00  0.00           H  
HETATM   39  H7  UNL     1       3.012  -2.311  -1.266  1.00  0.00           H  
HETATM   40  H8  UNL     1       2.764  -1.492   0.930  1.00  0.00           H  
HETATM   41  H9  UNL     1       0.959  -1.409  -2.031  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.515  -1.179  -2.130  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.464   0.409   1.618  1.00  0.00           H  
HETATM   44  H12 UNL     1      -6.672  -1.740   0.834  1.00  0.00           H  
HETATM   45  H13 UNL     1      -6.542  -1.782  -2.645  1.00  0.00           H  
HETATM   46  H14 UNL     1      -7.353  -0.270  -1.070  1.00  0.00           H  
HETATM   47  H15 UNL     1      -8.404   0.256   0.728  1.00  0.00           H  
HETATM   48  H16 UNL     1      -6.387   2.078  -0.838  1.00  0.00           H  
HETATM   49  H17 UNL     1      -6.017   1.048  -2.677  1.00  0.00           H  
HETATM   50  H18 UNL     1      -3.937   2.039  -0.237  1.00  0.00           H  
HETATM   51  H19 UNL     1      -6.056   2.534   1.173  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.511   0.288   1.864  1.00  0.00           H  
HETATM   53  H21 UNL     1       1.513  -0.843   2.634  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.525   0.658   2.973  1.00  0.00           H  
HETATM   55  H23 UNL     1       1.982   2.032   1.830  1.00  0.00           H  
HETATM   56  H24 UNL     1       3.037   0.940   2.743  1.00  0.00           H  
HETATM   57  H25 UNL     1       2.775   1.354  -0.194  1.00  0.00           H  
HETATM   58  H26 UNL     1       4.710  -0.437   1.376  1.00  0.00           H  
HETATM   59  H27 UNL     1       4.671   2.618   0.985  1.00  0.00           H  
HETATM   60  H28 UNL     1       5.267   1.619   2.406  1.00  0.00           H  
HETATM   61  H29 UNL     1       6.775   2.517   0.147  1.00  0.00           H  
HETATM   62  H30 UNL     1       7.325   1.402   1.511  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   28   31
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6   27   40
CONECT    6    7    7   24
CONECT    7    8   41
CONECT    8    9    9   42
CONECT    9   10   23
CONECT   10   11
CONECT   11   12   21   43
CONECT   12   13
CONECT   13   14   17   44
CONECT   14   15   15   16
CONECT   16   45
CONECT   17   18   19   46
CONECT   18   47
CONECT   19   20   21   48
CONECT   20   49
CONECT   21   22   50
CONECT   22   51
CONECT   23   24   24   52
CONECT   24   25
CONECT   25   26   53   54
CONECT   26   27   55   56
CONECT   27   28   57
CONECT   28   29   58
CONECT   29   30   59   60
CONECT   30   31   61   62
CONECT   31   32   32
END

HMDB0004483
     RDKit          3D
Estrone glucuronide
 62 66  0  0  0  0  0  0  0  0999 V2000
    4.6558    1.3418   -1.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.2766   -0.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7266   -1.1009   -1.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2431   -1.2212   -1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5272   -0.7893    0.1113 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0797   -0.6963   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3881   -1.0404   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9761   -0.9110   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378   -0.4346   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893   -0.3188   -0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0108    0.1282    0.6970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9045   -0.8524    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225   -1.1306    0.2426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5228   -2.0307   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3602   -2.4899   -1.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4520   -2.4060   -1.8406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7010    0.0692   -0.2441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4678    0.5572    0.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7903    1.1454   -0.7539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2883    0.8759   -2.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046    1.3987    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2207    2.0702    1.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0939    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397   -0.2249    1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    0.1380    2.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.9582    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    0.5875    0.5953 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4705    0.4805    0.8066 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1641    1.6980    1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868    1.5698    0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5171    0.4831   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4518   -0.0969   -0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    2.3185   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401    1.4041   -2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    1.1620   -2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1685   -1.2749   -2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -1.8304   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.7230   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -2.3115   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -1.4918    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9588   -1.4092   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5154   -1.1795   -2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    0.4093    1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6724   -1.7399    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5423   -1.7821   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3531   -0.2704   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4043    0.2562    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3874    2.0775   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0167    1.0485   -2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9367    2.0391   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561    2.5343    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    0.2884    1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129   -0.8435    2.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250    0.6583    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    2.0320    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    0.9396    2.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    1.3538   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7100   -0.4369    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.6177    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666    1.6187    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7746    2.5167    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3252    1.4023    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 28  2  1  0
 31  2  1  0
 27  5  1  0
 24  6  1  0
 21 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  1
  7 41  1  0
  8 42  1  0
 11 43  1  1
 13 44  1  1
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  6
 20 49  1  0
 21 50  1  6
 22 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  6
 28 58  1  1
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Estrone 3-glucosiduronic acid	ChEBI
Estrone 3-glucuronide	ChEBI
Estrone beta-D-glucuronide	ChEBI
Estrone 3-glucosiduronate	Generator
Estrone b-D-glucuronide	Generator
Estrone β-D-glucuronide	Generator
Estrone beta-delta-glucuronide	HMDB
Estrone-3-glucosiduronic acid	HMDB
Estrone-3-glucuronide	HMDB
Estrone-3-glucosiduronate	HMDB

Chemical Formula

C₂₄H₃₀O₈

Average Molecular Weight

446.4902

Monoisotopic Molecular Weight

446.194067936

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

estrone-3-glucuronide

CAS Registry Number

2479-90-5

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1

InChI Key

FJAZVHYPASAQKM-JBAURARKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Steroid-glucuronide-skeleton
Estrane-skeleton
17-oxosteroid
Oxosteroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Tetralin
Beta-hydroxy acid
Pyran
Fatty acyl
Oxane
Benzenoid
Monosaccharide
Hydroxy acid
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C18 steroids (estrogens) and derivatives (C11133 )
Glucuronides (C11133 )
Glucuronides (LMST05010011 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0004483)

Epithelium

Epidermis (HMDB: HMDB0004483)

Muscle tissue

Skeletal muscle (HMDB: HMDB0004483)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004483)

Organ

Gland

Adrenal Gland (HMDB: HMDB0004483)

Cell

Fibroblasts (HMDB: HMDB0004483)
Neuron (HMDB: HMDB0004483)

Excreta

Biofluid or Excreta

Urine (PMID: 6460495)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0004483)

Source

Endogenous

Endogenous (HMDB: HMDB0004483)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Estrone Metabolism (PathBank: SMP0087272)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	254.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	215.742	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000275

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.92	ALOGPS
logP	2.36	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.09 m³·mol⁻¹	ChemAxon
Polarizability	46.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	200.413	31661259
DarkChem	[M-H]-	196.564	31661259
DeepCCS	[M-2H]-	238.436	30932474
DeepCCS	[M+Na]+	212.598	30932474
AllCCS	[M+H]+	205.2	32859911
AllCCS	[M+H-H2O]+	203.4	32859911
AllCCS	[M+NH4]+	206.9	32859911
AllCCS	[M+Na]+	207.4	32859911
AllCCS	[M-H]-	199.8	32859911
AllCCS	[M+Na-2H]-	200.5	32859911
AllCCS	[M+HCOO]-	201.5	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.	5.28 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6699 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2275.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	174.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	464.8 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	524.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	162.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	987.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	506.2 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	1409.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	344.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	189.4 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	110.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estrone glucuronide	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]	4083.3	Standard polar	33892256
Estrone glucuronide	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]	3736.3	Standard non polar	33892256
Estrone glucuronide	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]	4049.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estrone glucuronide,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3893.7	Semi standard non polar	33892256
Estrone glucuronide,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3916.5	Semi standard non polar	33892256
Estrone glucuronide,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3907.3	Semi standard non polar	33892256
Estrone glucuronide,1TMS,isomer #4	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3869.9	Semi standard non polar	33892256
Estrone glucuronide,1TMS,isomer #5	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3764.5	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3880.8	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #10	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3710.9	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3901.5	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3906.6	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #4	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3714.2	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #5	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3881.4	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #6	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3913.7	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #7	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3733.8	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #8	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3883.9	Semi standard non polar	33892256
Estrone glucuronide,2TMS,isomer #9	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3721.6	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CCC2=O	3911.8	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #10	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3696.5	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3919.5	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3710.9	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #4	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3934.6	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #5	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3705.7	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #6	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3703.4	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #7	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3920.2	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #8	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3697.4	Semi standard non polar	33892256
Estrone glucuronide,3TMS,isomer #9	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3698.8	Semi standard non polar	33892256
Estrone glucuronide,4TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	3934.2	Semi standard non polar	33892256
Estrone glucuronide,4TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3705.1	Semi standard non polar	33892256
Estrone glucuronide,4TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3715.1	Semi standard non polar	33892256
Estrone glucuronide,4TMS,isomer #4	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3723.9	Semi standard non polar	33892256
Estrone glucuronide,4TMS,isomer #5	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3704.1	Semi standard non polar	33892256
Estrone glucuronide,5TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3738.6	Semi standard non polar	33892256
Estrone glucuronide,5TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	3803.6	Standard non polar	33892256
Estrone glucuronide,5TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	4058.8	Standard polar	33892256
Estrone glucuronide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@H]1O	4153.6	Semi standard non polar	33892256
Estrone glucuronide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)O[C@H](C(=O)O)[C@H]1O	4176.9	Semi standard non polar	33892256
Estrone glucuronide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	4163.5	Semi standard non polar	33892256
Estrone glucuronide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O	4151.4	Semi standard non polar	33892256
Estrone glucuronide,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)=CC=C4[C@H]3CC[C@]12C	4016.6	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	4401.5	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O	4222.8	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4389.6	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4388.4	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)=CC=C4[C@H]3CC[C@]12C	4223.6	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@@H]1O[Si](C)(C)C(C)(C)C	4394.5	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	4409.1	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)=CC=C4[C@H]3CC[C@]12C	4239.9	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	4401.7	Semi standard non polar	33892256
Estrone glucuronide,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	4228.4	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	4616.5	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	4427.1	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	4599.7	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	4422.9	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C(C)(C)C	4597.2	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	4414.2	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)=CC=C4[C@H]3CC[C@]12C	4400.3	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	4604.3	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	4403.9	Semi standard non polar	33892256
Estrone glucuronide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC2=CC=C3C(=C2)CC[C@@H]2[C@@H]3CC[C@]3(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	4415.0	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Ovary
Pancreas
Placenta
Prostate
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Estrone Metabolism		Not Available

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

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0014 +/- 0.00043 umol/mmol creatinine	Adult (>18 years old)	Male	Severe coronary artery disease	6460495	details
Urine	Detected and Quantified	0.0013 +/- 0.0003 umol/mmol creatinine	Adult (>18 years old)	Male	Minor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms	6460495	details

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

FDB021803

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

VMH ID

ESTRONEGLC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Werschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.

Material Safety Data Sheet (MSDS)

Not Available

General References

Luu-The V, Tremblay P, Labrie F: Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women. Mol Endocrinol. 2006 Feb;20(2):437-43. Epub 2005 Sep 15. [PubMed:16166196 ]
Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2. [PubMed:15522925 ]
Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200. [PubMed:3160310 ]
Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
Ivell R, Balvers M, Anand RJ, Paust HJ, McKinnell C, Sharpe R: Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. Endocrinology. 2003 Jul;144(7):3130-7. [PubMed:12810569 ]
Baum LW: Sex, hormones, and Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 2005 Jun;60(6):736-43. [PubMed:15983176 ]
Reutman SR, LeMasters GK, Kesner JS, Shukla R, Krieg EF Jr, Knecht EA, Lockey JE: Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age. Fertil Steril. 2002 Aug;78(2):383-91. [PubMed:12137878 ]
Harrison CA, Gossiel F, Bullock AJ, Sun T, Blumsohn A, Mac Neil S: Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. Br J Dermatol. 2006 Mar;154(3):401-10. [PubMed:16445767 ]
Ritvos O, Voutilainen R: Regulation of aromatase cytochrome P-450 and 17 beta-hydroxysteroid dehydrogenase messenger ribonucleic acid levels in choriocarcinoma cells. Endocrinology. 1992 Jan;130(1):61-7. [PubMed:1309352 ]
Kley HK: Plasma-estrogens and liver cirrhosis. Z Gastroenterol. 1979 Jul;17(7):406-12. [PubMed:224606 ]
Puranen T, Poutanen M, Ghosh D, Vihko P, Vihko R: Characterization of structural and functional properties of human 17 beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis. Mol Endocrinol. 1997 Jan;11(1):77-86. [PubMed:8994190 ]
Ueno T, Tamura S, Frels WI, Shou M, Gonzalez FJ, Kimura S: A transgenic mouse expressing human CYP1A2 in the pancreas. Biochem Pharmacol. 2000 Sep 15;60(6):857-63. [PubMed:10930541 ]
Schindler AE: Steroid metabolism in the gonads of a patient with testicular feminization. II. Metabolism of c19- and c18-steroids in vitro. Endokrinologie. 1976 Mar;67(1):14-9. [PubMed:1244196 ]
Carruba G, Cocciadiferro L, Bellavia V, Rizzo S, Tsatsanis C, Spandidos D, Muti P, Smith C, Mehta P, Castagnetta L: Intercellular communication and human hepatocellular carcinoma. Ann N Y Acad Sci. 2004 Dec;1028:202-12. [PubMed:15650246 ]
Authors unspecified: Temporal relationships between indices of the fertile period. Fertil Steril. 1983 May;39(5):647-55. [PubMed:6840308 ]
Cribb AE, Knight MJ, Dryer D, Guernsey J, Hender K, Tesch M, Saleh TM: Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer Epidemiol Biomarkers Prev. 2006 Mar;15(3):551-8. [PubMed:16537715 ]
Siiteri PK: Adipose tissue as a source of hormones. Am J Clin Nutr. 1987 Jan;45(1 Suppl):277-82. [PubMed:3541569 ]
Kenny AM, Fabregas G, Song C, Biskup B, Bellantonio S: Effects of testosterone on behavior, depression, and cognitive function in older men with mild cognitive loss. J Gerontol A Biol Sci Med Sci. 2004 Jan;59(1):75-8. [PubMed:14718489 ]
Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. [PubMed:12866733 ]
Beaudoin C, Bonenfant M, Tremblay Y: Regulation of cytochrome P450 cholesterol side-chain cleavage, 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4 isomerase type 1 and estradiol-17 beta-hydroxysteroid dehydrogenase mRNA levels by calcium in human choriocarcinoma JEG-3 cells. Mol Cell Endocrinol. 1997 Sep 30;133(1):63-71. [PubMed:9359473 ]
Bidlingmaier F, Strom TM, Dorr HG, Eisenmenger W, Knorr D: Estrone and estradiol concentrations in human ovaries, testes, and adrenals during the first two years of life. J Clin Endocrinol Metab. 1987 Nov;65(5):862-7. [PubMed:3667883 ]
Liu P, Higuchi WI, Ghanem AH, Good WR: Transport of beta-estradiol in freshly excised human skin in vitro: diffusion and metabolism in each skin layer. Pharm Res. 1994 Dec;11(12):1777-84. [PubMed:7899244 ]
Bray GA: The underlying basis for obesity: relationship to cancer. J Nutr. 2002 Nov;132(11 Suppl):3451S-3455S. [PubMed:12421869 ]
Iannuzzi-Sucich M, Prestwood KM, Kenny AM: Prevalence of sarcopenia and predictors of skeletal muscle mass in healthy, older men and women. J Gerontol A Biol Sci Med Sci. 2002 Dec;57(12):M772-7. [PubMed:12456735 ]
Kley HK, Kruskemper HL, Keck E: Estrone and estradiol in patients with cirrhosis of the liver: effects of ACTH and dexamethasone. J Clin Endocrinol Metab. 1976 Sep;43(3):557-60. [PubMed:182710 ]
Eichner SF, Timpe EM: Urinary-based ovulation and pregnancy: point-of-care testing. Ann Pharmacother. 2004 Feb;38(2):325-31. Epub 2003 Dec 30. [PubMed:14742773 ]
Collins WP: The evolution of reference methods to monitor ovulation. Am J Obstet Gynecol. 1991 Dec;165(6 Pt 2):1994-6. [PubMed:1755456 ]

Only showing the first 10 proteins. There are 22 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

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:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. 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

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

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:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Showing metabocard for Estrone glucuronide (HMDB0004483)

MOL for HMDB0004483 (Estrone glucuronide)

3D MOL for HMDB0004483 (Estrone glucuronide)

3D SDF for HMDB0004483 (Estrone glucuronide)

3D-SDF for HMDB0004483 (Estrone glucuronide)

PDB for HMDB0004483 (Estrone glucuronide)

3D PDB for HMDB0004483 (Estrone glucuronide)

SMILES for HMDB0004483 (Estrone glucuronide)

INCHI for HMDB0004483 (Estrone glucuronide)

Structure for HMDB0004483 (Estrone glucuronide)

3D Structure for HMDB0004483 (Estrone glucuronide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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