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CHEBI:4743 - ecgonine

ChEBI IDCHEBI:4743
ChEBI Nameecgonine
Stars
DefinitionA 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.
Last Modified27 January 2016
DownloadsMolfile
FormulaC9H15NO3
Net Charge0
Average Mass185.223
Monoisotopic Mass185.10519
SMILES[H][C@]12CC[C@]([H])([C@@H](C(=O)O)[C@@H](O)C1)N2C
InChIInChI=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
InChIKeyPHMBVCPLDPDESM-FKSUSPILSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
EcgonineKEGG COMPOUND
(-)-EcgonineChemIDplus
1-EcgonineChemIDplus
3β-hydroxy-2β-tropanecarboxylic acidChemIDplus
[1R*-(Exo,exo)]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acidNIST Chemistry WebBook
3β-hydroxy-1αH,5αH-tropane-2β-carboxylic acidNIST Chemistry WebBook
Manual XrefsDatabases
C10858KEGG COMPOUND
DB01525DrugBank
EcgonineWikipedia
C00002291KNApSAcK
Registry NumbersSources
Reaxys:83293Reaxys
CAS:481-37-8KEGG COMPOUND
CAS:481-37-8NIST Chemistry WebBook
Citations