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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

2013-05-17 01:25:09 UTC

Update Date

2021-09-14 15:46:39 UTC

HMDB ID

HMDB0060498

Secondary Accession Numbers

HMDB60498

Metabolite Identification

Common Name

NNAL-N-glucuronide

Description

NNAL-N-glucuronide belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond. NNAL-N-glucuronide is a strong basic compound (based on its pKa). These are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities.

Structure

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


  Mrv1652303102016592D          

 27 28  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 14 16  1  6  0  0  0
 18  1  1  0  0  0  0
 18  6  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  2  0  0  0  0
 19  8  1  0  0  0  0
 15 19  1  6  0  0  0
 20 10  1  0  0  0  0
 11 21  1  6  0  0  0
 12 22  1  1  0  0  0
 13 23  1  1  0  0  0
 24 16  2  0  0  0  0
 25 16  1  0  0  0  0
 26 17  2  0  0  0  0
 27 14  1  0  0  0  0
 27 15  1  0  0  0  0
M  CHG  1  19   1
M  END

HMDB0060498
     RDKit          3D
NNAL-N-glucuronide
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.8109    0.4519   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170    0.0342   -0.9201 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.2907   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -1.3208    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.3186    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.6069    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -1.9229    0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428    0.2431    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2384    1.4180    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    2.0983    1.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    1.6074    0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    0.4514    0.2281 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5197   -0.0353   -0.2377 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.7285   -1.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.6685   -1.3683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0325    1.9339   -0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    2.8489   -0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4155    2.1278   -0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0730   -0.5482   -0.8198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0939   -1.6070   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -1.0396    0.4938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5941   -1.1458    1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -0.1382    0.9630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7281   -0.8053    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.2163   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923    0.8809   -1.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856    2.0501   -1.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5354    0.9544    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3552    1.1771   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4784   -0.4092   -0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861   -1.5403   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9613   -2.0178   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984   -1.2405    1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -2.3591    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.6886    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.4197    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6344   -0.4728   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8554   -2.4430   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.7614    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    3.0226    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    2.1786    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123   -1.0711   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219    0.6465   -2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8743    2.1683   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678   -0.2916   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414   -2.4599   -1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -2.0448    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.9858    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093    0.8398    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602   -0.0810    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774   -1.1479   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
  2 26  1  0
 26 27  2  0
 25  8  1  0
 23 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
M  CHG  1  12   1
M  END


  Mrv1652303102016592D          

 27 28  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 14 16  1  6  0  0  0
 18  1  1  0  0  0  0
 18  6  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  2  0  0  0  0
 19  8  1  0  0  0  0
 15 19  1  6  0  0  0
 20 10  1  0  0  0  0
 11 21  1  6  0  0  0
 12 22  1  1  0  0  0
 13 23  1  1  0  0  0
 24 16  2  0  0  0  0
 25 16  1  0  0  0  0
 26 17  2  0  0  0  0
 27 14  1  0  0  0  0
 27 15  1  0  0  0  0
M  CHG  1  19   1
M  END
> <DATABASE_ID>
HMDB0060498

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCCC(O)C1=C[N+](=CC=C1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N3O8/c1-18(17-26)6-3-5-10(20)9-4-2-7-19(8-9)15-13(23)11(21)12(22)14(27-15)16(24)25/h2,4,7-8,10-15,20-23H,3,5-6H2,1H3/p+1/t10?,11-,12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
VSVYJUYJFLYYSI-UKOUFMKDSA-O

> <FORMULA>
C16H24N3O8

> <MOLECULAR_WEIGHT>
386.3771

> <EXACT_MASS>
386.156339759

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.55235863804371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-5.729768971861792

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.704968547439012

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7073893872848984

> <JCHEM_PKA_STRONGEST_BASIC>
3.5069232418432534

> <JCHEM_POLAR_SURFACE_AREA>
163.99999999999997

> <JCHEM_REFRACTIVITY>
91.66359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060498
     RDKit          3D
NNAL-N-glucuronide
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.8109    0.4519   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170    0.0342   -0.9201 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.2907   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -1.3208    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.3186    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.6069    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -1.9229    0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428    0.2431    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2384    1.4180    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    2.0983    1.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    1.6074    0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    0.4514    0.2281 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5197   -0.0353   -0.2377 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.7285   -1.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.6685   -1.3683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0325    1.9339   -0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    2.8489   -0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4155    2.1278   -0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0730   -0.5482   -0.8198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0939   -1.6070   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -1.0396    0.4938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5941   -1.1458    1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -0.1382    0.9630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7281   -0.8053    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.2163   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923    0.8809   -1.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856    2.0501   -1.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5354    0.9544    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3552    1.1771   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4784   -0.4092   -0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861   -1.5403   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9613   -2.0178   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984   -1.2405    1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -2.3591    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.6886    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.4197    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6344   -0.4728   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8554   -2.4430   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.7614    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    3.0226    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    2.1786    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123   -1.0711   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219    0.6465   -2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8743    2.1683   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678   -0.2916   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414   -2.4599   -1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -2.0448    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.9858    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093    0.8398    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602   -0.0810    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774   -1.1479   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
  2 26  1  0
 26 27  2  0
 25  8  1  0
 23 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
M  CHG  1  12   1
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.001   8.470   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.667   9.240   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+1
HETATM   20  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -12.003  11.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -12.003   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -13.337   9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    4    7                                                       
CONECT    3    5    6                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    3   18                                                       
CONECT    7    2   19                                                       
CONECT    8    9   19                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   20                                                  
CONECT   11   12   13   21                                                  
CONECT   12   11   14   22                                                  
CONECT   13   11   15   23                                                  
CONECT   14   12   16   27                                                  
CONECT   15   13   19   27                                                  
CONECT   16   14   24   25                                                  
CONECT   17   18   26                                                       
CONECT   18    1    6   17                                                  
CONECT   19    7    8   15                                                  
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24   16                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0060498
HETATM    1  C1  UNL     1       6.811   0.452  -0.220  1.00  0.00           C  
HETATM    2  N1  UNL     1       5.617   0.034  -0.920  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.098  -1.291  -0.668  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.585  -1.321   0.744  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.491  -0.319   1.010  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.339  -0.607   0.112  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.913  -1.923   0.408  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.143   0.243   0.441  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.238   1.418   1.146  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.063   2.098   1.380  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.142   1.607   0.922  1.00  0.00           C  
HETATM   12  N2  UNL     1      -1.234   0.451   0.228  1.00  0.00           N1+
HETATM   13  C10 UNL     1      -2.520  -0.035  -0.238  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.062   0.728  -1.245  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.412   0.668  -1.368  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.032   1.934  -0.912  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.279   2.849  -0.502  1.00  0.00           O  
HETATM   18  O4  UNL     1      -6.415   2.128  -0.927  1.00  0.00           O  
HETATM   19  C13 UNL     1      -5.073  -0.548  -0.820  1.00  0.00           C  
HETATM   20  O5  UNL     1      -5.094  -1.607  -1.755  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.589  -1.040   0.494  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.594  -1.146   1.451  1.00  0.00           O  
HETATM   23  C15 UNL     1      -3.467  -0.138   0.963  1.00  0.00           C  
HETATM   24  O7  UNL     1      -2.728  -0.805   1.966  1.00  0.00           O  
HETATM   25  C16 UNL     1      -0.075  -0.216  -0.002  1.00  0.00           C  
HETATM   26  N3  UNL     1       4.992   0.881  -1.806  1.00  0.00           N  
HETATM   27  O8  UNL     1       5.386   2.050  -1.997  1.00  0.00           O  
HETATM   28  H1  UNL     1       6.535   0.954   0.745  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.355   1.177  -0.880  1.00  0.00           H  
HETATM   30  H3  UNL     1       7.478  -0.409  -0.009  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.286  -1.540  -1.356  1.00  0.00           H  
HETATM   32  H5  UNL     1       5.961  -2.018  -0.774  1.00  0.00           H  
HETATM   33  H6  UNL     1       5.398  -1.240   1.498  1.00  0.00           H  
HETATM   34  H7  UNL     1       4.166  -2.359   0.897  1.00  0.00           H  
HETATM   35  H8  UNL     1       3.930   0.689   0.794  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.237  -0.420   2.095  1.00  0.00           H  
HETATM   37  H10 UNL     1       2.634  -0.473  -0.928  1.00  0.00           H  
HETATM   38  H11 UNL     1       1.855  -2.443  -0.435  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.204   1.761   1.485  1.00  0.00           H  
HETATM   40  H13 UNL     1       0.125   3.023   1.934  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.047   2.179   1.130  1.00  0.00           H  
HETATM   42  H15 UNL     1      -2.412  -1.071  -0.619  1.00  0.00           H  
HETATM   43  H16 UNL     1      -4.622   0.647  -2.484  1.00  0.00           H  
HETATM   44  H17 UNL     1      -6.874   2.168  -0.024  1.00  0.00           H  
HETATM   45  H18 UNL     1      -6.168  -0.292  -0.691  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.241  -2.460  -1.290  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.099  -2.045   0.329  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.414  -1.986   1.959  1.00  0.00           H  
HETATM   49  H22 UNL     1      -3.809   0.840   1.305  1.00  0.00           H  
HETATM   50  H23 UNL     1      -2.260  -0.081   2.477  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.177  -1.148  -0.565  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   26
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   25
CONECT    9   10   39
CONECT   10   11   11   40
CONECT   11   12   41
CONECT   12   13   25   25
CONECT   13   14   23   42
CONECT   14   15
CONECT   15   16   19   43
CONECT   16   17   17   18
CONECT   18   44
CONECT   19   20   21   45
CONECT   20   46
CONECT   21   22   23   47
CONECT   22   48
CONECT   23   24   49
CONECT   24   50
CONECT   25   51
CONECT   26   27   27
END

HMDB0060498
     RDKit          3D
NNAL-N-glucuronide
 51 52  0  0  0  0  0  0  0  0999 V2000
    6.8109    0.4519   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170    0.0342   -0.9201 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -1.2907   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -1.3208    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906   -0.3186    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.6069    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -1.9229    0.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428    0.2431    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2384    1.4180    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627    2.0983    1.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    1.6074    0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    0.4514    0.2281 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5197   -0.0353   -0.2377 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.7285   -1.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.6685   -1.3683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0325    1.9339   -0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    2.8489   -0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4155    2.1278   -0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0730   -0.5482   -0.8198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0939   -1.6070   -1.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5885   -1.0396    0.4938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5941   -1.1458    1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -0.1382    0.9630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7281   -0.8053    1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -0.2163   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923    0.8809   -1.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3856    2.0501   -1.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5354    0.9544    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3552    1.1771   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4784   -0.4092   -0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861   -1.5403   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9613   -2.0178   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984   -1.2405    1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -2.3591    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.6886    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.4197    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6344   -0.4728   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8554   -2.4430   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.7614    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    3.0226    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    2.1786    1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123   -1.0711   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219    0.6465   -2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8743    2.1683   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1678   -0.2916   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414   -2.4599   -1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -2.0448    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4144   -1.9858    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093    0.8398    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2602   -0.0810    2.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774   -1.1479   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12 25  2  0
  2 26  1  0
 26 27  2  0
 25  8  1  0
 23 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
M  CHG  1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄N₃O₈

Average Molecular Weight

386.3771

Monoisotopic Molecular Weight

386.156339759

IUPAC Name

1-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1lambda5-pyridin-1-ylium

Traditional Name

1-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-3-{1-hydroxy-4-[methyl(nitroso)amino]butyl}-1lambda5-pyridin-1-ylium

CAS Registry Number

Not Available

SMILES

CN(CCCC(O)C1=C[N+](=CC=C1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)N=O

InChI Identifier

InChI=1S/C16H23N3O8/c1-18(17-26)6-3-5-10(20)9-4-2-7-19(8-9)15-13(23)11(21)12(22)14(27-15)16(24)25/h2,4,7-8,10-15,20-23H,3,5-6H2,1H3/p+1/t10?,11-,12-,13+,14-,15+/m0/s1

InChI Key

VSVYJUYJFLYYSI-UKOUFMKDSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-glucuronides

Alternative Parents

Substituents

N-glucuronide
Glycosyl compound
N-glycosyl compound
Beta-hydroxy acid
Hydroxy acid
Oxane
Pyran
Pyridine
Pyridinium
Heteroaromatic compound
Secondary alcohol
Organic n-nitroso compound
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Azacycle
Polyol
Carboxylic acid
Organic nitroso compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Aromatic alcohol
Organic cation
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: HMDB0060498)

Organ

Liver (HMDB: HMDB0060498)
Kidney (HMDB: HMDB0060498)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060498)

Source

Endogenous

Endogenous (HMDB: HMDB0060498)

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

Lagomorph

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Poultry

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)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)

Equine

Horse (FooDB: FOOD00378)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0060498)

Physical Properties

State

Not Available

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	0.83 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.7	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	3.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	91.66 m³·mol⁻¹	ChemAxon
Polarizability	38.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	192.778	31661259
DarkChem	[M-H]-	188.732	31661259
DeepCCS	[M+H]+	178.514	30932474
DeepCCS	[M-H]-	176.237	30932474
DeepCCS	[M-2H]-	209.476	30932474
DeepCCS	[M+Na]+	184.289	30932474
AllCCS	[M+H]+	189.0	32859911
AllCCS	[M+H-H2O]+	186.5	32859911
AllCCS	[M+NH4]+	191.3	32859911
AllCCS	[M+Na]+	192.0	32859911
AllCCS	[M-H]-	189.3	32859911
AllCCS	[M+Na-2H]-	189.2	32859911
AllCCS	[M+HCOO]-	189.2	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.	1.96 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3676 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1546.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	187.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	304.7 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	370.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	256.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	718.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	112.9 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	1241.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	203.9 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	96.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
NNAL-N-glucuronide	CN(CCCC(O)C1=C[N+](=CC=C1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)N=O	4066.9	Standard polar	33892256
NNAL-N-glucuronide	CN(CCCC(O)C1=C[N+](=CC=C1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)N=O	3096.4	Standard non polar	33892256
NNAL-N-glucuronide	CN(CCCC(O)C1=C[N+](=CC=C1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)N=O	3471.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
NNAL-N-glucuronide,1TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3144.0	Semi standard non polar	33892256
NNAL-N-glucuronide,1TMS,isomer #2	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3138.9	Semi standard non polar	33892256
NNAL-N-glucuronide,1TMS,isomer #3	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3126.8	Semi standard non polar	33892256
NNAL-N-glucuronide,1TMS,isomer #4	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3119.5	Semi standard non polar	33892256
NNAL-N-glucuronide,1TMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3132.7	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3073.8	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #10	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3064.1	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #2	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3062.7	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #3	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3052.3	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #4	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3048.5	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3093.7	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #6	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3081.3	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #7	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3079.4	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #8	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3079.5	Semi standard non polar	33892256
NNAL-N-glucuronide,2TMS,isomer #9	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3062.2	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3057.2	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #10	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3049.7	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #2	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3047.9	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #3	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3034.0	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #4	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)=C1)N=O	3045.6	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #5	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3040.1	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #6	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3032.5	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #7	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[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]2O)=C1)N=O	3082.5	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #8	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3064.4	Semi standard non polar	33892256
NNAL-N-glucuronide,3TMS,isomer #9	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3067.2	Semi standard non polar	33892256
NNAL-N-glucuronide,4TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[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]2O)=C1)N=O	3057.1	Semi standard non polar	33892256
NNAL-N-glucuronide,4TMS,isomer #2	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)=C1)N=O	3041.8	Semi standard non polar	33892256
NNAL-N-glucuronide,4TMS,isomer #3	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3022.0	Semi standard non polar	33892256
NNAL-N-glucuronide,4TMS,isomer #4	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1)N=O	3048.3	Semi standard non polar	33892256
NNAL-N-glucuronide,4TMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[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]2O[Si](C)(C)C)=C1)N=O	3068.7	Semi standard non polar	33892256
NNAL-N-glucuronide,5TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=C[N+]([C@@H]2O[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]2O[Si](C)(C)C)=C1)N=O	3052.0	Semi standard non polar	33892256
NNAL-N-glucuronide,1TBDMS,isomer #1	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3443.3	Semi standard non polar	33892256
NNAL-N-glucuronide,1TBDMS,isomer #2	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3410.3	Semi standard non polar	33892256
NNAL-N-glucuronide,1TBDMS,isomer #3	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3413.3	Semi standard non polar	33892256
NNAL-N-glucuronide,1TBDMS,isomer #4	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3406.9	Semi standard non polar	33892256
NNAL-N-glucuronide,1TBDMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3427.2	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #1	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)=C1)N=O	3591.3	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #10	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3577.9	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #2	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3566.4	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #3	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3576.0	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #4	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3567.5	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3588.1	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #6	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[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]2O)=C1)N=O	3577.6	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #7	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3564.0	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #8	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3593.9	Semi standard non polar	33892256
NNAL-N-glucuronide,2TBDMS,isomer #9	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3562.8	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #1	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)=C1)N=O	3756.3	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #10	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3726.1	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #2	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3765.9	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #3	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3738.8	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #4	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[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]2O)=C1)N=O	3738.8	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #5	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3715.8	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #6	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3716.1	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #7	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3748.2	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #8	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3728.3	Semi standard non polar	33892256
NNAL-N-glucuronide,3TBDMS,isomer #9	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3736.8	Semi standard non polar	33892256
NNAL-N-glucuronide,4TBDMS,isomer #1	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1)N=O	3901.6	Semi standard non polar	33892256
NNAL-N-glucuronide,4TBDMS,isomer #2	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3879.1	Semi standard non polar	33892256
NNAL-N-glucuronide,4TBDMS,isomer #3	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3874.9	Semi standard non polar	33892256
NNAL-N-glucuronide,4TBDMS,isomer #4	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=C[N+]([C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3887.8	Semi standard non polar	33892256
NNAL-N-glucuronide,4TBDMS,isomer #5	CN(CCCC(O)C1=CC=C[N+]([C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1)N=O	3893.0	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 - NNAL-N-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0670-9166000000-8f44995fdafb2501b0a0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NNAL-N-glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-053r-5552029000-2a55c360a53bfb22a025	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NNAL-N-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - NNAL-N-glucuronide 10V, Positive-QTOF	splash10-014i-0019000000-429b4a59db9309b38ee7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NNAL-N-glucuronide 20V, Positive-QTOF	splash10-0ik9-3669000000-15643d1116ce8d95cce8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NNAL-N-glucuronide 40V, Positive-QTOF	splash10-0ik9-3940000000-27e11619af4a2591fa7c	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB034585

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53297451

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

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

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-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

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

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

Show all enzymes and transporters

Showing metabocard for NNAL-N-glucuronide (HMDB0060498)

MOL for HMDB0060498 (NNAL-N-glucuronide)

3D MOL for HMDB0060498 (NNAL-N-glucuronide)

3D SDF for HMDB0060498 (NNAL-N-glucuronide)

3D-SDF for HMDB0060498 (NNAL-N-glucuronide)

PDB for HMDB0060498 (NNAL-N-glucuronide)

3D PDB for HMDB0060498 (NNAL-N-glucuronide)

SMILES for HMDB0060498 (NNAL-N-glucuronide)

INCHI for HMDB0060498 (NNAL-N-glucuronide)

Structure for HMDB0060498 (NNAL-N-glucuronide)

3D Structure for HMDB0060498 (NNAL-N-glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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