Human Metabolome Database Version 3.5

Showing metabocard for trans-3-Hydroxycotinine glucuronide (HMDB01204)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-06-10 10:20:26 -0600
HMDB ID HMDB01204
Secondary Accession Numbers None
Metabolite Identification
Common Name trans-3-Hydroxycotinine glucuronide
Description 3-Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. It is also excreted as a glucuronide conjugate (3HC-Gluc). 3HC and 3HC-Gluc account for 40-60% of the nicotine dose in urine.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3'-Hydroxycotnine-glucuronide
  2. 3HC-Gluc
  3. trans-3-Hydroxycotinine-glucuronide
Chemical Formula C16H20N2O8
Average Molecular Weight 368.3386
Monoisotopic Molecular Weight 368.121965626
IUPAC Name (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
Traditional IUPAC Name (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number 132929-88-5
SMILES [H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8?,9-,10+,11+,12-,13+,16-/m1/s1
InChI Key WALNNKZUGHYSCT-QBYCBOKUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Glucuronic Acid Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • Glucuronic Acid Derivatives
  • O-glycosyl Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Beta Hydroxy Acid
  • Carboxamide Group
  • Carboxylic Acid
  • Hexose Monosaccharide
  • Lactam
  • Nicotine
  • Oxane
  • Pyridine
  • Pyrrolidine
  • Pyrrolidinylpyridine
  • Pyrrolidone
  • Secondary Alcohol
  • Tertiary Carboxylic Acid Amide
Direct Parent Glucuronides
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 38.9 g/L ALOGPS
LogP -1.70 ALOGPS
LogP -3.3 ChemAxon
LogS -0.98 ALOGPS
pKa (strongest acidic) 3.23 ChemAxon
pKa (strongest basic) 4.8 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 149.65 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 83.01 ChemAxon
Polarizability 35.29 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 DBMET00522 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022490
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID CPD-2752 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01204 Link_out
Metagene Link HMDB01204 Link_out
METLIN ID 6080 Link_out
PubChem Compound 53477725 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Rop PP, Grimaldi F, Oddoze C, Viala A: Determination of nicotine and its main metabolites in urine by high-performance liquid chromatography. J Chromatogr. 1993 Feb 26;612(2):302-9. Pubmed: 8468389 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 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