Human Metabolome Database Version 3.5

Showing metabocard for Ecgonine methyl ester (HMDB06406)

Record Information
Version 3.5
Creation Date 2007-05-22 23:46:51 -0600
Update Date 2013-05-29 13:43:42 -0600
HMDB ID HMDB06406
Secondary Accession Numbers None
Metabolite Identification
Common Name Ecgonine methyl ester
Description Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85% for ecgonine methyl ester could be obtained from urine. (PMID:1298401 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. Methyl ecgonine
Chemical Formula C10H17NO3
Average Molecular Weight 199.2469
Monoisotopic Molecular Weight 199.120843415
IUPAC Name methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Traditional IUPAC Name methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Registry Number 7143-09-1
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 Key QIQNNBXHAYSQRY-ABIFROTESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteropolycyclic Compounds
Class Piperidines
Sub Class Piperidinecarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Tropane alkaloids(KEGG)
  • Tropanes
Substituents
  • Beta Hydroxy Acid
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Pyrrolidine
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Piperidinecarboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 587 g/L ALOGPS
LogP 0.14 ALOGPS
LogP -0.21 ChemAxon
LogS 0.47 ALOGPS
pKa (strongest acidic) 14.6 ChemAxon
pKa (strongest basic) 9.04 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 49.77 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 51.34 ChemAxon
Polarizability 20.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.237 +/- 0.0150 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023911
KNApSAcK ID Not Available
Chemspider ID 391939 Link_out
KEGG Compound ID C12448 Link_out
BioCyc ID Not Available
BiGG ID 2267774 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06406 Link_out
Metagene Link HMDB06406 Link_out
METLIN ID Not Available
PubChem Compound 443844 Link_out
PDB ID Not Available
ChEBI ID 708640 Link_out
References
Synthesis Reference Kline, 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 Link_out

Enzymes
Name: Lysosomal acid lipase/cholesteryl ester hydrolase
Reactions: Not Available
Gene Name: LIPA
Uniprot ID: P38571 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions:
Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cocaine esterase
Reactions:
Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details
Gene Name: CES2
Uniprot ID: O00748 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carboxylesterase 5A
Reactions: Not Available
Gene Name: CES5A
Uniprot ID: Q6NT32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA