Benzoylecgonine (CHEM019232)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:56:10 UTC
Update Date2016-11-09 01:15:57 UTC
Accession NumberCHEM019232
Identification
Common NameBenzoylecgonine
ClassSmall Molecule
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. It is the main pharmaceutical ingredient in the investigational drug Esterom, a topical solution used for the relief of muscle pain that is not FDA approved or on the market in the United States.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-BenzoylecgonineChEBI
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acidChEBI
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidChEBI
BCGChEBI
BEGChEBI
O-Benzoyl-(-)-ecgonineChEBI
O-BenzoylecgonineChEBI
(1R,2R,3S,5S)-8-Methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylateGenerator
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylateGenerator
Benzoylecgonine, (1R-(2-endo,3-exo))-isomerMeSH
Benzoyl ecgonineMeSH
BenzoylecgonineChEBI
Ecgonine benzoic acidGenerator
Chemical FormulaC16H19NO4
Average Molecular Mass289.326 g/mol
Monoisotopic Mass289.131 g/mol
CAS Registry Number519-09-5
IUPAC Name(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Traditional Namebenzoylecgonine
SMILES[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(O)=O)N2C
InChI IdentifierInChI=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-RFQIPJPRSA-N
Chemical Taxonomy
Description 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
  • 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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability29.93 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-63cd666addb0ec431ed9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1940000000-7bbbc9c1090789aebcc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-380a14d86c89a1ac7706Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-3bdddf883ffa7af32815Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1690000000-7832e304ed3fe450a24eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi9-3910000000-9ad134e82515eb476d60Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01515
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002280
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEcgonine_benzoate
Chemspider IDNot Available
ChEBI ID41001
PubChem Compound ID448223
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11095584
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11303043
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11384570
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11469854
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12908939
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14606999
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15885702
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16389661
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17610217
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18819113
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=18974960
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=19127949