Bovine Metabolome Database: Showing metabocard for Ecgonine methyl ester (BMDB0006406)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:21:58 UTC

Update Date

2020-04-22 15:17:25 UTC

BMDB ID

BMDB0006406

Secondary Accession Numbers

BMDB06406

Metabolite Identification

Common Name

Ecgonine methyl ester

Description

Ecgonine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl ecgonine	Kegg

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 Name

ecgonine methyl ester

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

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Tropane alkaloids (C12448 )

Ontology

Status

Expected but not 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
logP	0.14	ALOGPS
logP	-0.21	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.34 m³·mol⁻¹	ChemAxon
Polarizability	20.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9500000000-cf2ddf077b00040815cb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-007k-9320000000-2c7c73b58d1886e618c5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0090000000-6bb519514639540eac7e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0f89-0950000000-117ad116d5ac14a5be9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-507c3f3bafb08a0393f6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-daa82fab29c3bc26425a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0g5i-0900000000-56c0d97c8ede7a0f5121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-daa82fab29c3bc26425a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-fffbd1cb1619e5f92d43	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0g5i-0900000000-56c0d97c8ede7a0f5121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0v5i-0900000000-a539dd19738540ffeecd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0v5i-0900000000-de76b46915632e6c01da	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-687b3144e289411d4082	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-22aa62b28391bb713265	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0950000000-ffcfa77b222d15829aaa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-e3fcef6498db4fb940cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0950000000-efcb591e326d6b910be4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1920000000-3866ea5e436094dba234	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-3900000000-482ddc1485526a169412	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-2bd0a82ed0375eb83de6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00rw-0900000000-3bc21f157c0540443956	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-1900000000-d566bd6e77d93dbf8b71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-10dc01597bf9d10d45eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0900000000-0e30c6026623a71a7a3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-6900000000-94cf39d3cb9ec7c8a4be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-90ea4410b322d690d160	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2790000000-9c3dd1d85b04ba825e6a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Endoplasmic reticulum

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0006406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

2267774

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443844

PDB ID

Not Available

ChEBI ID

708640

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

Not Available

Showing metabocard for Ecgonine methyl ester (BMDB0006406)

Structure for BMDB0006406 (Ecgonine methyl ester)