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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:54 UTC
Update Date2017-12-07 04:29:05 UTC
HMDB IDHMDB0041836
Secondary Accession Numbers
  • HMDB41836
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=1S/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-/m0/s1
InChI KeyGVGYEFKIHJTNQZ-HOAMVYINSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.39 m³·mol⁻¹ChemAxon
Polarizability30.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9300000000-2744be9f1b527a82cbd4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4j-9610000000-67e335ee9149b74d3c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0490000000-b318fb29702eb5424d35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0950000000-12bed261b67b5013666eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9800000000-3a17195c76e52677183cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0190000000-083b9c17aad363499aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1490000000-2fc324c6b5bed2c47666View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bi-3900000000-deb0d1b5a143fa9057b1View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      METLIN IDNot Available
      PubChem Compound442997
      PDB IDNot Available
      ChEBI ID41001
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available