BCG

3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID

Created:	2003-09-15
Last modified:	2020-06-05

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2 entries where BCG is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	40
Chiral Atom Count	4
Bond Count	42
Aromatic Bond Count	6

2D diagram of BCG

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Chemical Component Summary
Name	3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID
Synonyms	BENZOYLECGONINE
Systematic Name (OpenEye OEToolkits)	(1R,2R,3S,5S,8S)-8-methyl-3-(phenylcarbonyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Formula	C₁₆ H₁₉ N O₄
Molecular Weight	289.326
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C3C1N(C)C(CC1)CC3OC(=O)c2ccccc2
SMILES	CACTVS	3.341	CN1[CH]2CC[CH]1[CH]([CH](C2)OC(=O)c3ccccc3)C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	CN1C2CCC1C(C(C2)OC(=O)c3ccccc3)C(=O)O
Canonical SMILES	CACTVS	3.341	CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[N@]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O
InChI	InChI	1.03	InChI=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
InChIKey	InChI	1.03	GVGYEFKIHJTNQZ-RFQIPJPRSA-N

Drug Info: DrugBank

DrugBank ID	DB01515
Name	Benzoylecgonine
Groups	illicit experimental
Description	Benzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. It is the main pharmaceutical ingredient in the investigational drug Esterom, a topical solution used for the relief of muscle pain that is not FDA approved or on the market in the United States. [A18735]
Synonyms	O-benzoyl-(-)-ecgonine Benzoylecgonine 3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid O-benzoylecgonine (-)-benzoylecgonine Ecgonine benzoate (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Categories	Alkaloids Aza Compounds Azabicyclo Compounds Tropanes
CAS number	519-09-5

Related Resource References

Resource Name	Reference
PubChem	24916772, 448223
ChEMBL	CHEMBL1231248
ChEBI	CHEBI:41001

RCSB PDB Core Operations are funded by the U.S. National Science Foundation (DBI-2321666), the US Department of Energy (DE-SC0019749), and the National Cancer Institute, National Institute of Allergy and Infectious Diseases, and National Institute of General Medical Sciences of the National Institutes of Health under grant R01GM157729.