cocaine   

GtoPdb Ligand ID: 2286

cocaine is an approved drug
Comment: Cocaine is a tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca. Topically applied cocaine has local anesthetic effects, causing loss of feeling or numbness. It also causes vasoconstriction.
There is no information on the US Drugs@FDA website regarding marketing approval for formulations of this drug.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 55.84
Molecular weight 303.15
XLogP 2.31
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C1C(CC2N(C1CC2)C)OC(=O)c1ccccc1
Isomeric SMILES COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
InChI InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
InChI Key ZPUCINDJVBIVPJ-LJISPDSOSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes
IUPAC Name
methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Database Links
BindingDB Ligand 50006232
CAS Registry No. 50-36-2
ChEBI CHEBI:27958
ChEMBL Ligand CHEMBL370805
DrugBank Ligand DB00907
DrugCentral Ligand 723
GtoPdb PubChem SID 135652677
PubChem CID 446220
RCSB PDB Ligand COC
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Wikipedia Cocaine