CHEBI:4743 - ecgonine

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ChEBI Name ecgonine
ChEBI ID CHEBI:4743
Definition A tropane alkaloid that consists of tropane bearing carboxy and hydroxy substituents at positions 2 and 3 respectively and having (1R,2R,3S,5S)-configuration. It is both a metabolite of and a precursor to cocaine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H15NO3
Net Charge 0
Average Mass 185.22030
Monoisotopic Mass 185.105
InChI InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1
InChIKey PHMBVCPLDPDESM-FKSUSPILSA-N
SMILES [H][C@]12CC[C@]([H])([C@H]([C@@H](O)C1)C(O)=O)N2C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ecgonine (CHEBI:4743) has role metabolite (CHEBI:25212)
ecgonine (CHEBI:4743) has role mouse metabolite (CHEBI:75771)
ecgonine (CHEBI:4743) is a 2-hydroxy monocarboxylic acid (CHEBI:49302)
ecgonine (CHEBI:4743) is a tropane alkaloid (CHEBI:37332)
Incoming O-benzoylecgonine 5-carboxypentyl ester (CHEBI:63312) has functional parent ecgonine (CHEBI:4743)
ecgonine benzoate (CHEBI:41001) has functional parent ecgonine (CHEBI:4743)
ecgonine methyl ester (CHEBI:31529) has functional parent ecgonine (CHEBI:4743)
hapten GNL (CHEBI:63227) has functional parent ecgonine (CHEBI:4743)
ioflupane I123 (CHEBI:68855) has functional parent ecgonine (CHEBI:4743)
IUPAC Name
(1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Synonyms Sources
(-)-Ecgonine ChemIDplus
1-Ecgonine ChemIDplus
3β-hydroxy-1αH,5αH-tropane-2β-carboxylic acid NIST Chemistry WebBook
3β-hydroxy-2β-tropanecarboxylic acid ChemIDplus
[1R*-(Exo,exo)]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid NIST Chemistry WebBook
Ecgonine KEGG COMPOUND
Database Links Databases
C00002291 KNApSAcK
C10858 KEGG COMPOUND
DB01525 DrugBank
Ecgonine Wikipedia
View more database links
Registry Numbers Types Sources
481-37-8 CAS Registry Number KEGG COMPOUND
481-37-8 CAS Registry Number NIST Chemistry WebBook
83293 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11469854 PubMed citation Europe PMC
20077067 PubMed citation Europe PMC
22018173 PubMed citation Europe PMC
Last Modified
27 January 2016