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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 05:46:51 UTC
Update Date2021-09-14 15:45:58 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 exists in all living organisms, ranging from bacteria to humans. Ecgonine methyl ester has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make ecgonine methyl ester a potential biomarker for the consumption of these foods. Ecgonine methyl ester is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Ecgonine methyl ester.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.11431661259
DarkChem[M-H]-143.64231661259
DeepCCS[M+H]+147.79730932474
DeepCCS[M-H]-145.43930932474
DeepCCS[M-2H]-178.99730932474
DeepCCS[M+Na]+154.08530932474
AllCCS[M+H]+146.632859911
AllCCS[M+H-H2O]+142.632859911
AllCCS[M+NH4]+150.232859911
AllCCS[M+Na]+151.332859911
AllCCS[M-H]-146.332859911
AllCCS[M+Na-2H]-146.932859911
AllCCS[M+HCOO]-147.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ecgonine methyl esterCOC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C2523.2Standard polar33892256
Ecgonine methyl esterCOC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C1495.3Standard non polar33892256
Ecgonine methyl esterCOC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C1564.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ecgonine methyl ester,1TMS,isomer #1COC(=O)[C@@H]1C2CCC(C[C@@H]1O[Si](C)(C)C)N2C1578.4Semi standard non polar33892256
Ecgonine methyl ester,1TBDMS,isomer #1COC(=O)[C@@H]1C2CCC(C[C@@H]1O[Si](C)(C)C(C)(C)C)N2C1787.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine methyl ester GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-9500000000-cf2ddf077b00040815cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine methyl ester GC-MS (1 TMS) - 70eV, Positivesplash10-007k-9320000000-2c7c73b58d1886e618c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ecgonine methyl ester GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-6bb519514639540eac7e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOFsplash10-0f89-0950000000-117ad116d5ac14a5be9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-507c3f3bafb08a0393f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-daa82fab29c3bc26425a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester LC-ESI-QTOF , positive-QTOFsplash10-0g5i-0900000000-56c0d97c8ede7a0f51212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOFsplash10-001i-0900000000-daa82fab29c3bc26425a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 30V, Positive-QTOFsplash10-001i-0900000000-fffbd1cb1619e5f92d432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOFsplash10-0g5i-0900000000-56c0d97c8ede7a0f51212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOFsplash10-0v5i-0900000000-a539dd19738540ffeecd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 50V, Positive-QTOFsplash10-0v5i-0900000000-de76b46915632e6c01da2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 30V, Positive-QTOFsplash10-001i-0900000000-687b3144e289411d40822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOFsplash10-001i-0900000000-22aa62b28391bb7132652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOFsplash10-0f89-0950000000-ffcfa77b222d15829aaa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOFsplash10-0udi-0090000000-e3fcef6498db4fb940cc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Negative-QTOFsplash10-0002-0900000000-2bd0a82ed0375eb83de62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Negative-QTOFsplash10-00rw-0900000000-3bc21f157c05404439562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Negative-QTOFsplash10-00dl-1900000000-d566bd6e77d93dbf8b712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Negative-QTOFsplash10-0002-0900000000-10dc01597bf9d10d45eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Negative-QTOFsplash10-014j-0900000000-0e30c6026623a71a7a3e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Negative-QTOFsplash10-00dl-6900000000-94cf39d3cb9ec7c8a4be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOFsplash10-0ue9-0950000000-efcb591e326d6b910be42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOFsplash10-0ue9-1920000000-3866ea5e436094dba2342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 40V, Positive-QTOFsplash10-0fk9-3900000000-482ddc1485526a1694122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 10V, Positive-QTOFsplash10-0udi-0090000000-90ea4410b322d690d1602021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ecgonine methyl ester 20V, Positive-QTOFsplash10-0udi-2790000000-9c3dd1d85b04ba825e6a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDC00051754
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 IDEGME
MarkerDB IDNot Available
Good Scents 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