Human Metabolome Database Version 3.5

Showing metabocard for Nicotine glucuronide (HMDB01272)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-06-10 10:21:35 -0600
HMDB ID HMDB01272
Secondary Accession Numbers None
Metabolite Identification
Common Name Nicotine glucuronide
Description Nicotine glucuronidation results in an N-quaternary glucuronide in humans. This reaction is catalyzed by uridine diphosphate-glucuronosyltransferase (UGT) enzyme(s) producing (S)-nicotine-N-beta-glucuronide (Nicotine-Gluc). About 3-5% of nicotine is converted to Nicotine-Gluc and excreted in urine in humans.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-1-alpha-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-Pyridinium inner salt
  2. (S)-1-alpha-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt
  3. (S)-1-alpha-delta-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-Pyridinium inner salt
  4. (S)-1-alpha-delta-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt
  5. 1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-Pyridinium
  6. 1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-Pyridinium
  7. 1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-Pyridinium
  8. 1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-Pyridinium
  9. Nicotine glucuronide
  10. Nicotine N-glucuronide
  11. Nicotine-Glucuronide
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]-1$l^{5}-pyridin-1-ylium
Traditional IUPAC Name 1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1$l^{5}-pyridin-1-ylium
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
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Sugar Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Beta Hydroxy Acid
  • Carboxylic Acid Salt
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glyco Amino Acid
  • Glycosyl Compound
  • Hexose Monosaccharide
  • N Glycosyl Compound
  • Nicotine
  • Oxane
  • Pyridine
  • Pyridinium
  • Pyrrolidine
  • Pyrrolidinylpyridine
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Pyranoid Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental 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
Predicted Properties
Property Value Source
Water Solubility 8.02 g/L ALOGPS
LogP -1.65 ALOGPS
LogP -7.3 ChemAxon
LogS -1.69 ALOGPS
pKa (strongest acidic) 2.52 ChemAxon
pKa (strongest basic) 7.42 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 117.17 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 94.18 ChemAxon
Polarizability 33.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID DBMET00524 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022526
KNApSAcK ID Not Available
Chemspider ID 2299987 Link_out
KEGG Compound ID Not Available
BioCyc ID CPD-2744 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01272 Link_out
Metagene Link HMDB01272 Link_out
METLIN ID 6127 Link_out
PubChem Compound 3035848 Link_out
PDB ID Not Available
ChEBI ID 63860 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: UDP-glucuronosyltransferase 2B28
Reactions: Not Available
Gene Name: UGT2B28
Uniprot ID: Q9BY64 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B4
Reactions: Not Available
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions: Not Available
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B10
Reactions: Not Available
Gene Name: UGT2B10
Uniprot ID: P36537 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions: Not Available
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B15
Reactions: Not Available
Gene Name: UGT2B15
Uniprot ID: P54855 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A1
Reactions: Not Available
Gene Name: UGT2A1
Uniprot ID: Q9Y4X1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions: Not Available
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions: Not Available
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-3
Reactions: Not Available
Gene Name: UGT1A3
Uniprot ID: P35503 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions: Not Available
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions: Not Available
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-5
Reactions: Not Available
Gene Name: UGT1A5
Uniprot ID: P35504 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B11
Reactions: Not Available
Gene Name: UGT2B11
Uniprot ID: O75310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-glucuronidase
Reactions: Not Available
Gene Name: GUSB
Uniprot ID: P08236 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A3
Reactions: Not Available
Gene Name: UGT2A3
Uniprot ID: Q6UWM9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_f
Reactions: Not Available
Gene Name: UGT1A10
Uniprot ID: Q5DT02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_e
Reactions: Not Available
Gene Name: UGT1A8
Uniprot ID: Q5DSZ6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP glycosyltransferase 1 family polypeptide A7
Reactions: Not Available
Gene Name: UGT1A7
Uniprot ID: Q5DSZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA