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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19) Show 19 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:47:06 UTC

HMDB ID

HMDB0001272

Secondary Accession Numbers

HMDB01272

Metabolite Identification

Common Name

Nicotine glucuronide

Description

Nicotine glucuronide belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Nicotine glucuronide is a very strong basic compound (based on its pKa). nicotine glucuronide and uridine 5'-diphosphate can be biosynthesized from nicotine and uridine diphosphate glucuronic acid; which is mediated by the enzymes UDP-glucuronosyltransferase 1-4 and UDP-glucuronosyltransferase 1-9. In humans, nicotine glucuronide is involved in nicotine metabolism pathway. An N-glycosylpyridine that is the N-alpha-D-glucosiduronyl derivative of (S)-nicotine.

Structure

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

HMDB0001272
     RDKit          3D
Nicotine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -2.5534   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -1.1413    0.1736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583   -0.7306    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.5670   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4430    0.6483   -1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.3169   -0.7456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4155    0.4480   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    1.0550    1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932    1.7604    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    1.8563    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    1.2730    0.1219 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1627    1.4431   -0.3214 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0017    1.6655    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    0.6276    1.5233 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6519    0.9405    2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.3297    3.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    1.8969    1.6683 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4184   -0.7206    0.9367 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9196   -1.6967    1.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794   -0.9229   -0.3527 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2893   -1.9209   -1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3479   -1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2159    0.2413   -2.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414    0.5814   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0138   -2.8498   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -2.8302   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -3.1203    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8362   -0.5355    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -1.5204   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875    0.5489   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7874    1.4473    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.3357   -2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685    1.7063   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587   -0.9133   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.9763    1.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    2.2357    2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    2.4446    1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    2.3780   -0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062    0.5814    2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769   -1.0249    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156   -1.7835    2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317   -1.2462   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -2.4644   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8267    0.5831   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.7307   -2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.1032   -1.4460 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  2  0
  6  2  1  0
 24  7  1  0
 22 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  8 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  6
 14 39  1  1
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
 24 46  1  0
M  CHG  2  11   1  17  -1
M  END


  Mrv0541 02231219012D          

 24 26  0  0  1  0            999 V2000
   11.6189   -6.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0023   -8.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168   -8.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0023   -9.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313   -9.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4515   -7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8995   -8.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0390   -7.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313   -8.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1457   -8.2266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0023  -11.9392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7168  -12.3517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0023  -11.1142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4313  -11.9392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7168  -10.7017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1457  -12.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168   -9.8767    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.2320   -7.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2878  -12.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7168  -13.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2878  -10.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1457  -13.1767    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.8603  -11.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4313  -11.1142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4 17  2  0  0  0  0
  5  9  2  0  0  0  0
  5 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 18  1  0  0  0  0
 10  9  1  1  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 19  1  6  0  0  0
 12 14  1  0  0  0  0
 12 20  1  1  0  0  0
 13 15  1  0  0  0  0
 13 21  1  1  0  0  0
 14 16  1  6  0  0  0
 14 24  1  0  0  0  0
 15 17  1  1  0  0  0
 15 24  1  0  0  0  0
 16 22  1  0  0  0  0
 16 23  2  0  0  0  0
M  CHG  2  17   1  22  -1
M  END
> <DATABASE_ID>
HMDB0001272

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1

> <INCHI_KEY>
SAWAIULJDYFLPD-SOAFEQHCSA-N

> <FORMULA>
C16H22N2O6

> <MOLECULAR_WEIGHT>
338.3557

> <EXACT_MASS>
338.147786446

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
33.41630530952722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-7.262402522114074

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.709548854847307

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5186103009766083

> <JCHEM_PKA_STRONGEST_BASIC>
7.4181638395435066

> <JCHEM_POLAR_SURFACE_AREA>
117.17

> <JCHEM_REFRACTIVITY>
94.17699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicotine glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001272
     RDKit          3D
Nicotine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -2.5534   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -1.1413    0.1736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583   -0.7306    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.5670   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4430    0.6483   -1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.3169   -0.7456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4155    0.4480   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    1.0550    1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932    1.7604    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    1.8563    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    1.2730    0.1219 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1627    1.4431   -0.3214 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0017    1.6655    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    0.6276    1.5233 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6519    0.9405    2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.3297    3.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    1.8969    1.6683 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4184   -0.7206    0.9367 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9196   -1.6967    1.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794   -0.9229   -0.3527 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2893   -1.9209   -1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3479   -1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2159    0.2413   -2.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414    0.5814   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0138   -2.8498   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -2.8302   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -3.1203    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8362   -0.5355    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -1.5204   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875    0.5489   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7874    1.4473    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.3357   -2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685    1.7063   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587   -0.9133   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.9763    1.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    2.2357    2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    2.4446    1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    2.3780   -0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062    0.5814    2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769   -1.0249    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156   -1.7835    2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317   -1.2462   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -2.4644   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8267    0.5831   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.7307   -2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.1032   -1.4460 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  2  0
  6  2  1  0
 24  7  1  0
 22 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  8 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  6
 14 39  1  1
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
 24 46  1  0
M  CHG  2  11   1  17  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      21.689 -12.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.671 -16.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.005 -15.356   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.671 -17.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.338 -17.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.109 -14.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.079 -15.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.339 -13.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.338 -16.126   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.672 -15.356   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.671 -22.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.005 -23.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.671 -20.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.338 -22.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005 -19.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.672 -23.057   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      20.005 -18.437   0.000  0.00  0.00           N+1
HETATM   18  N   UNK     0      22.833 -13.825   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      17.337 -23.057   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      20.005 -24.597   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      17.337 -19.977   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      22.672 -24.597   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      24.006 -22.287   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      21.338 -20.747   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   17                                                       
CONECT    5    9   17                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6   18                                                       
CONECT    9    3    5   10                                                  
CONECT   10    7    9   18                                                  
CONECT   11   12   13   19                                                  
CONECT   12   11   14   20                                                  
CONECT   13   11   15   21                                                  
CONECT   14   12   16   24                                                  
CONECT   15   13   17   24                                                  
CONECT   16   14   22   23                                                  
CONECT   17    4    5   15                                                  
CONECT   18    1    8   10                                                  
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0001272
HETATM    1  C1  UNL     1      -3.109  -2.553  -0.138  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.194  -1.141   0.174  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.558  -0.731   0.208  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.680   0.567  -0.524  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.443   0.648  -1.359  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.480  -0.317  -0.746  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.416   0.448  -0.044  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.745   1.055   1.151  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.793   1.760   1.814  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.477   1.856   1.285  1.00  0.00           C  
HETATM   11  N2  UNL     1       0.822   1.273   0.122  1.00  0.00           N1+
HETATM   12  C10 UNL     1       2.163   1.443  -0.321  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.002   1.665   0.737  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.334   0.628   1.523  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.652   0.940   2.172  1.00  0.00           C  
HETATM   16  O2  UNL     1       5.008   0.330   3.212  1.00  0.00           O  
HETATM   17  O3  UNL     1       5.522   1.897   1.668  1.00  0.00           O1-
HETATM   18  C13 UNL     1       3.418  -0.721   0.937  1.00  0.00           C  
HETATM   19  O4  UNL     1       2.920  -1.697   1.834  1.00  0.00           O  
HETATM   20  C14 UNL     1       2.679  -0.923  -0.353  1.00  0.00           C  
HETATM   21  O5  UNL     1       3.289  -1.921  -1.113  1.00  0.00           O  
HETATM   22  C15 UNL     1       2.726   0.348  -1.158  1.00  0.00           C  
HETATM   23  O6  UNL     1       2.216   0.241  -2.422  1.00  0.00           O  
HETATM   24  C16 UNL     1      -0.141   0.581  -0.512  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.014  -2.850  -0.738  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.192  -2.830  -0.678  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.187  -3.120   0.813  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.836  -0.535   1.283  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.243  -1.520  -0.188  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.588   0.549  -1.173  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.787   1.447   0.150  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.699   0.336  -2.390  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.068   1.706  -1.316  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.959  -0.913  -1.535  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.746   0.976   1.562  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.052   2.236   2.750  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.186   2.445   1.883  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.192   2.378  -0.953  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.606   0.581   2.387  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.477  -1.025   0.758  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.616  -1.783   2.539  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.632  -1.246  -0.188  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.920  -2.464  -0.557  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.827   0.583  -1.280  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.145  -0.731  -2.644  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.103   0.103  -1.446  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    6
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34
CONECT    7    8    8   24
CONECT    8    9   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   24   24
CONECT   12   13   22   38
CONECT   13   14
CONECT   14   15   18   39
CONECT   15   16   16   17
CONECT   18   19   20   40
CONECT   19   41
CONECT   20   21   22   42
CONECT   21   43
CONECT   22   23   44
CONECT   23   45
CONECT   24   46
END

HMDB0001272
     RDKit          3D
Nicotine glucuronide
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.1092   -2.5534   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -1.1413    0.1736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583   -0.7306    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.5670   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4430    0.6483   -1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.3169   -0.7456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4155    0.4480   -0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    1.0550    1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932    1.7604    1.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    1.8563    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223    1.2730    0.1219 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1627    1.4431   -0.3214 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0017    1.6655    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    0.6276    1.5233 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6519    0.9405    2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.3297    3.2118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215    1.8969    1.6683 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4184   -0.7206    0.9367 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9196   -1.6967    1.8344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794   -0.9229   -0.3527 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2893   -1.9209   -1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3479   -1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2159    0.2413   -2.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414    0.5814   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0138   -2.8498   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -2.8302   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -3.1203    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8362   -0.5355    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -1.5204   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875    0.5489   -1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7874    1.4473    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    0.3357   -2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0685    1.7063   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587   -0.9133   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    0.9763    1.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    2.2357    2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    2.4446    1.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    2.3780   -0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062    0.5814    2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769   -1.0249    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156   -1.7835    2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317   -1.2462   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -2.4644   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8267    0.5831   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.7307   -2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1028    0.1032   -1.4460 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  2  0
  6  2  1  0
 24  7  1  0
 22 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  8 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  6
 14 39  1  1
 18 40  1  6
 19 41  1  0
 20 42  1  1
 21 43  1  0
 22 44  1  6
 23 45  1  0
 24 46  1  0
M  CHG  2  11   1  17  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	ChEBI
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylate	ChEBI
Nicotine N-glucuronide	ChEBI
(S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	Generator
(S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	Generator
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acid	Generator
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt	HMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt	HMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt	HMDB
1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium	HMDB
1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium	HMDB
1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium	HMDB
1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium	HMDB
Nicotine-glucuronide	HMDB

Chemical Formula

C₁₆H₂₂N₂O₆

Average Molecular Weight

338.3557

Monoisotopic Molecular Weight

338.147786446

IUPAC Name

1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium

Traditional Name

nicotine glucuronide

CAS Registry Number

152306-59-7

SMILES

CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O

InChI Identifier

InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1

InChI Key

SAWAIULJDYFLPD-SOAFEQHCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside triphosphates

Alternative Parents

Substituents

Purine ribonucleoside triphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Hydroxypyrimidine
Alkyl phosphate
Pyrimidine
Monosaccharide
Phosphoric acid ester
N-substituted imidazole
Organic phosphoric acid derivative
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosine 5'-phosphate (CHEBI:15996 )
purine ribonucleoside 5'-triphosphate (CHEBI:15996 )
Ribonucleotides (C00044 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001272)

Organ

Liver (HMDB: HMDB0001272)
Kidney (HMDB: HMDB0001272)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001272)

Cellular substructure

Cytoplasm (HMDB: HMDB0001272)

Source

Endogenous

Endogenous (HMDB: HMDB0001272)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotine Metabolism Pathway (HMDB: HMDB0001272)
Nicotine Metabolism Pathway (PathBank: SMP0000628)

Drug action pathway

Nicotine Action Pathway (HMDB: HMDB0001272)
Nicotine Action Pathway (PathBank: SMP0000431)

Role

Biological role

Drug metabolite (HMDB: HMDB0001272)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.02 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-7.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	7.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.17 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	180.431	32859911
AllCCS	[M-H]-	179.825	32859911
DeepCCS	[M+H]+	170.462	30932474
DeepCCS	[M-H]-	168.067	30932474
DeepCCS	[M-2H]-	201.091	30932474
DeepCCS	[M+Na]+	176.354	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	183.3	32859911
AllCCS	[M+Na]+	184.1	32859911
AllCCS	[M-H]-	179.8	32859911
AllCCS	[M+Na-2H]-	179.1	32859911
AllCCS	[M+HCOO]-	178.5	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.	1.08 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3766 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	215.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	583.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	190.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.8 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	291.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	741.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	624.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	50.1 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	742.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	164.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	718.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	446.7 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	183.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotine glucuronide	CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O	3706.0	Standard polar	33892256
Nicotine glucuronide	CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O	2740.3	Standard non polar	33892256
Nicotine glucuronide	CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O	2879.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nicotine glucuronide,1TMS,isomer #1	CN1CCC[C@H]1C1=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	2674.3	Semi standard non polar	33892256
Nicotine glucuronide,1TMS,isomer #2	CN1CCC[C@H]1C1=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	2691.4	Semi standard non polar	33892256
Nicotine glucuronide,1TMS,isomer #3	CN1CCC[C@H]1C1=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	2673.3	Semi standard non polar	33892256
Nicotine glucuronide,2TMS,isomer #1	CN1CCC[C@H]1C1=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	2702.4	Semi standard non polar	33892256
Nicotine glucuronide,2TMS,isomer #2	CN1CCC[C@H]1C1=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	2690.7	Semi standard non polar	33892256
Nicotine glucuronide,2TMS,isomer #3	CN1CCC[C@H]1C1=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	2700.9	Semi standard non polar	33892256
Nicotine glucuronide,3TMS,isomer #1	CN1CCC[C@H]1C1=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	2749.9	Semi standard non polar	33892256
Nicotine glucuronide,1TBDMS,isomer #1	CN1CCC[C@H]1C1=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	2910.2	Semi standard non polar	33892256
Nicotine glucuronide,1TBDMS,isomer #2	CN1CCC[C@H]1C1=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	2937.0	Semi standard non polar	33892256
Nicotine glucuronide,1TBDMS,isomer #3	CN1CCC[C@H]1C1=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	2914.3	Semi standard non polar	33892256
Nicotine glucuronide,2TBDMS,isomer #1	CN1CCC[C@H]1C1=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	3148.7	Semi standard non polar	33892256
Nicotine glucuronide,2TBDMS,isomer #2	CN1CCC[C@H]1C1=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	3151.4	Semi standard non polar	33892256
Nicotine glucuronide,2TBDMS,isomer #3	CN1CCC[C@H]1C1=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	3148.8	Semi standard non polar	33892256
Nicotine glucuronide,3TBDMS,isomer #1	CN1CCC[C@H]1C1=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	3383.0	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 - Nicotine glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9363000000-498032dac1d25a048f1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine glucuronide GC-MS (3 TMS) - 70eV, Positive	splash10-000l-6695530000-5f3cb4632382491d1884	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine 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 - Nicotine glucuronide 10V, Positive-QTOF	splash10-000i-0009000000-c0a6517967854466764f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 20V, Positive-QTOF	splash10-004r-3209000000-9c96a94c455824fbcb27	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 40V, Positive-QTOF	splash10-03xu-6911000000-358133c8eb23ea49be3b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 10V, Negative-QTOF	splash10-000i-0009000000-470460c450e2ce5dc00f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 20V, Negative-QTOF	splash10-000i-5594000000-c8f1d538ca13bdab946d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 40V, Negative-QTOF	splash10-0a4i-9200000000-83503a4041514150d674	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 10V, Positive-QTOF	splash10-000i-0209000000-45aaad3735689e97aa1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 20V, Positive-QTOF	splash10-03yr-0905000000-ca062e765a6a892950c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 40V, Positive-QTOF	splash10-001i-3910000000-d6d53f13a1744fd96f8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 10V, Negative-QTOF	splash10-000i-0229000000-8425edbf57e8743a529b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 20V, Negative-QTOF	splash10-06ri-5977000000-71e200566908d48e305d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine glucuronide 40V, Negative-QTOF	splash10-05fr-8941000000-0a955908878509d2a872	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Nicotine Action Pathway		Not Available
Nicotine Metabolism Pathway		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
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

FDB022526

KNApSAcK ID

Not Available

Chemspider ID

2299987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6127

PubChem Compound

3035848

PDB ID

Not Available

ChEBI ID

63860

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

Heavner DL, Richardson JD, Morgan WT, Ogden MW: Validation and application of a method for the determination of nicotine and five major metabolites in smokers' urine by solid-phase extraction and liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2005 May;19(4):312-28. [PubMed:15651085 ]
Tulunay OE, Hecht SS, Carmella SG, Zhang Y, Lemmonds C, Murphy S, Hatsukami DK: Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer Epidemiol Biomarkers Prev. 2005 May;14(5):1283-6. [PubMed:15894687 ]
Hecht SS, Carmella SG, Chen M, Dor Koch JF, Miller AT, Murphy SE, Jensen JA, Zimmerman CL, Hatsukami DK: Quantitation of urinary metabolites of a tobacco-specific lung carcinogen after smoking cessation. Cancer Res. 1999 Feb 1;59(3):590-6. [PubMed:9973205 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

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

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

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

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

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

References

Kuehl GE, Murphy SE: N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2003 Nov;31(11):1361-8. [PubMed:14570768 ]

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

References

Kaivosaari S, Toivonen P, Hesse LM, Koskinen M, Court MH, Finel M: Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10. Mol Pharmacol. 2007 Sep;72(3):761-8. Epub 2007 Jun 18. [PubMed:17576790 ]

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

References

Kaivosaari S, Toivonen P, Hesse LM, Koskinen M, Court MH, Finel M: Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10. Mol Pharmacol. 2007 Sep;72(3):761-8. Epub 2007 Jun 18. [PubMed:17576790 ]

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

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

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

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

References

Kuehl GE, Murphy SE: N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2003 Nov;31(11):1361-8. [PubMed:14570768 ]

Enzyme Details

10. UDP-glucuronosyltransferase 1-3

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

References

Kuehl GE, Murphy SE: N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2003 Nov;31(11):1361-8. [PubMed:14570768 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Showing metabocard for Nicotine glucuronide (HMDB0001272)

MOL for HMDB0001272 (Nicotine glucuronide)

3D MOL for HMDB0001272 (Nicotine glucuronide)

3D SDF for HMDB0001272 (Nicotine glucuronide)

3D-SDF for HMDB0001272 (Nicotine glucuronide)

PDB for HMDB0001272 (Nicotine glucuronide)

3D PDB for HMDB0001272 (Nicotine glucuronide)

SMILES for HMDB0001272 (Nicotine glucuronide)

INCHI for HMDB0001272 (Nicotine glucuronide)

Structure for HMDB0001272 (Nicotine glucuronide)

3D Structure for HMDB0001272 (Nicotine glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References