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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:09 UTC
HMDB IDHMDB0001272
Secondary Accession Numbers
  • HMDB01272
Metabolite Identification
Common NameNicotine glucuronide
DescriptionNicotine glucuronide belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 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 catalyzed by the enzymes UDP-glucuronosyltransferase 1-4 and UDP-glucuronosyltransferase 1-9. In humans, nicotine glucuronide is involved in nicotine metabolism pathway.
Structure
Data?1582752188
Synonyms
ValueSource
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltChEBI
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylateChEBI
Nicotine N-glucuronideChEBI
(S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltGenerator
(S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltGenerator
3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acidGenerator
(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner saltHMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner saltHMDB
(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner saltHMDB
1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridiniumHMDB
1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridiniumHMDB
1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridiniumHMDB
1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridiniumHMDB
Nicotine-glucuronideHMDB
Chemical FormulaC16H22N2O6
Average Molecular Weight338.3557
Monoisotopic Molecular Weight338.147786446
IUPAC Name1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium
Traditional Namenicotine glucuronide
CAS Registry Number152306-59-7
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 KeySAWAIULJDYFLPD-SOAFEQHCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Urea
  • 1,2-diol
  • Lactam
  • Dialkyl ether
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.02 g/LALOGPS
logP-1.6ALOGPS
logP-7.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)7.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.17 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.18 m³·mol⁻¹ChemAxon
Polarizability33.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9363000000-498032dac1d25a048f1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000l-6695530000-5f3cb4632382491d1884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-c0a6517967854466764fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-3209000000-9c96a94c455824fbcb27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-6911000000-358133c8eb23ea49be3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-470460c450e2ce5dc00fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-5594000000-c8f1d538ca13bdab946dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-83503a4041514150d674Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022526
KNApSAcK IDNot Available
Chemspider ID2299987
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6127
PubChem Compound3035848
PDB IDNot Available
ChEBI ID63860
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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.

Enzymes

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
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
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
  1. 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 ]
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
  1. 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 ]
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
  1. 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 ]
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
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
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
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
  1. 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 ]
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
  1. 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.