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Substrate Report for: Benzoylecgonine

Name Class
BenzoylecgonineTypeDrug
Not A/B H target
Alkaloid
Azabicyclo
Other_NameO-Benzoylecgonine
(-)-Benzoylecgonine
O-Benzoyl-(-)-ecgonine
Benzoylecgonine solution
Chemical_Nomenclature(1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
FormulaC16H19NO4
CAS_number519-09-5
MW289.32
PaperBrzezinski_1994_Biochem.Pharmacol_48_1747
Chen_2016_ACS.Chem.Biol_11_2186
CommentBenzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases (Brzezinski et al. 1994). It is excreted in the urine of cocaine users after processing in the liver. It is hydrolyzed by BCHE mutants (Chen et al. 2016)
Gene_locushuman-BCHE
rhosm-cocE
CID448223
FamilyBCHE
Cocaine_esterase
InChIKeyGVGYEFKIHJTNQZ-RFQIPJPRSA-N
CanonicalSMILESCN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)O
InChIInChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1

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Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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