Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-06-10 16:20:26 UTC
HMDB IDHMDB01204
Secondary Accession NumbersNone
Metabolite Identification
Common Nametrans-3-Hydroxycotinine glucuronide
Description3-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
Synonyms
  1. 3'-Hydroxycotnine-glucuronide
  2. 3HC-Gluc
  3. trans-3-Hydroxycotinine-glucuronide
Chemical FormulaC16H20N2O8
Average Molecular Weight368.3386
Monoisotopic Molecular Weight368.121965626
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 Number132929-88-5
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 KeyWALNNKZUGHYSCT-QBYCBOKUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassGlucuronic 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 ParentGlucuronides
Ontology
StatusExpected and Not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 solubility38.9 g/LALOGPS
logP-1.7ALOGPS
logP-3.3ChemAxon
logS-0.98ALOGPS
pKa (strongest acidic)3.23ChemAxon
pKa (strongest basic)4.8ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count9ChemAxon
hydrogen donor count4ChemAxon
polar surface area149.65ChemAxon
rotatable bond count4ChemAxon
refractivity83.01ChemAxon
polarizability35.29ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00522
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022490
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-2752
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01204
Metagene LinkHMDB01204
METLIN ID6080
PubChem Compound53477725
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot 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

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6