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Record Information
Version3.6
Creation Date2012-09-13 11:41:54 UTC
Update Date2016-02-11 03:55:37 UTC
HMDB IDHMDB41836
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzoyl ecgonine
DescriptionBenzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. [Wikipedia]
Structure
Thumb
Synonyms
ValueSource
(-)-BenzoylecgonineHMDB
(1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidHMDB
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acidHMDB
3-(BENZOYLOXY)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylIC ACIDHMDB
BCGHMDB
BEGHMDB
BenzoylecgonineHMDB
Benzoylecgonine hydrateHMDB
Benzoylecgonine solutionHMDB
BenzoylecogonineHMDB
Ecgonine benzoateHMDB
O-Benzoyl-(-)-ecgonineHMDB
O-BenzoylecgonineHMDB
Chemical FormulaC16H19NO4
Average Molecular Weight289.3264
Monoisotopic Molecular Weight289.131408101
IUPAC Name(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Traditional Name(2S,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
CAS Registry Number519-09-5
SMILES
[H][C@@]1(CC2CCC([C@@H]1C(O)=O)N2C)OC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11?,12?,13-,14-/s2
InChI KeyInChIKey=GVGYEFKIHJTNQZ-TZCSZHHPNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Tropane alkaloid
  • Piperidinecarboxylic acid
  • Benzylether
  • Benzoyl
  • N-alkylpyrrolidine
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Nutrient
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point195 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.82 mg/mLALOGPS
logP1.71ALOGPS
logP-0.59ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.39 m3·mol-1ChemAxon
Polarizability30.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00644
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID391300
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB41836
Metagene LinkHMDB41836
METLIN IDNot Available
PubChem Compound442997
PDB IDNot Available
ChEBI ID41001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available