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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 05:46:51 UTC
Update Date2020-02-26 21:26:23 UTC
HMDB IDHMDB0006406
Secondary Accession Numbers
  • HMDB06406
Metabolite Identification
Common NameEcgonine methyl ester
DescriptionEcgonine methyl ester, also known as methyl ecgonine, belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Ecgonine methyl ester is a major metabolite of cocaine. Ecgonine methyl ester is a very strong basic compound (based on its pKa). Ecgonine methyl ester exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752383
Synonyms
ValueSource
Methyl ecgonineKegg
Chemical FormulaC10H17NO3
Average Molecular Weight199.2469
Monoisotopic Molecular Weight199.120843415
IUPAC Namemethyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Traditional Nameecgonine methyl ester
CAS Registry Number7143-09-1
SMILES
COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C
InChI Identifier
InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1
InChI KeyQIQNNBXHAYSQRY-ABIFROTESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Piperidine
  • N-alkylpyrrolidine
  • Methyl ester
  • Pyrrolidine
  • Cyclic alcohol
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

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 Solubility587 g/LALOGPS
logP0.14ALOGPS
logP-0.21ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)14.6ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.34 m³·mol⁻¹ChemAxon
Polarizability20.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9500000000-cf2ddf077b00040815cbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007k-9320000000-2c7c73b58d1886e618c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-6bb519514639540eac7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f89-0950000000-117ad116d5ac14a5be9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-507c3f3bafb08a0393f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-daa82fab29c3bc26425aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0g5i-0900000000-56c0d97c8ede7a0f5121Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0950000000-efcb591e326d6b910be4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-1920000000-3866ea5e436094dba234Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-3900000000-482ddc1485526a169412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2bd0a82ed0375eb83de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rw-0900000000-3bc21f157c0540443956Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-1900000000-d566bd6e77d93dbf8b71Spectrum
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.237 +/- 0.0150 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023911
KNApSAcK IDNot Available
Chemspider ID391939
KEGG Compound IDC12448
BioCyc IDNot Available
BiGG ID2267774
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443844
PDB IDNot Available
ChEBI ID708640
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceKline, Richard Harry, Jr. The synthesis and pharmacological activity of 3-arylecgonine methyl ester and 3-carbamoyloxyecgonine methyl ester analogs: probes for the characterization of the dopaminergic cocaine receptor. (1991), 127 pp. CAN 116:21292 AN 1992:21292
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roy IM, Jefferies TM, Threadgill MD, Dewar GH: Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):943-8. [PubMed:1298401 ]

Enzymes

General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Molecular weight:
63925.82