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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:37 UTC
HMDB IDHMDB01427
Secondary Accession NumbersNone
Metabolite Identification
Common Name5'-Hydroxycotinine
Description5'-Hydroxycotinine is a hydroxylated derivative of cotinine. Cotinine is dervied from nicotine.
Structure
Thumb
Synonyms
ValueSource
AllohydroxycotinineMetaCyc
5-HydroxycotinineHMDB
Chemical FormulaC10H12N2O2
Average Molecular Weight192.2145
Monoisotopic Molecular Weight192.089877638
IUPAC Name(5R)-5-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Name5-hydroxycotinine
CAS Registry Number61192-50-5
SMILES
CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1
InChI KeyInChIKey=BBNHNZGTKSWIHD-SNVBAGLBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Nicotine
  • Alkaloid or derivatives
  • Pyrrolidinylpyridine
  • N-alkylpyrrolidine
  • 2-pyrrolidone
  • Pyrrolidone
  • Pyridine
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility90.2 mg/mLALOGPS
logP-0.31ALOGPS
logP-0.21ChemAxon
logS-0.33ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)4.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.43 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.86 m3·mol-1ChemAxon
Polarizability19.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Nicotine Metabolism PathwaySMP00628Not Available
Nicotine PathwaySMP00431Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022616
KNApSAcK IDNot Available
Chemspider ID7991265
KEGG Compound IDNot Available
BioCyc IDCPD-2751
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01427
Metagene LinkHMDB01427
METLIN ID6239
PubChem Compound9815515
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available