Showing metabocard for Ecgonine methyl ester (BMDB0006406)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:58 UTC
Update Date2020-04-22 15:17:25 UTC
BMDB IDBMDB0006406
Secondary Accession Numbers
  • BMDB06406
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 exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on Ecgonine methyl ester.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006406
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023911
KNApSAcK IDC00051754
Chemspider ID391939
KEGG Compound IDC12448
BioCyc IDNot Available
BiGG ID2267774
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443844
PDB IDNot Available
ChEBI ID708640
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 ReferencesNot Available