capsaicin   

GtoPdb Ligand ID: 2486

Synonyms: Qutenza®
capsaicin is an approved drug (EMA & FDA (2009))
Comment: Although capsaicin was approved by the US FDA in 2009, this compound was previously marketed so was not subject to a New Drug Application.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 58.56
Molecular weight 305.2
XLogP 4.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1cc(CNC(=O)CCCCC=CC(C)C)ccc1O
Isomeric SMILES COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChI InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChI Key YKPUWZUDDOIDPM-SOFGYWHQSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (EMA & FDA (2009))
IUPAC Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
International Nonproprietary Names
INN number INN
10145 capsaicin
Synonyms
Qutenza®
Comments
Although capsaicin was approved by the US FDA in 2009, this compound was previously marketed so was not subject to a New Drug Application.
Database Links
BindingDB Ligand 20461
CAS Registry No. 404-86-4
ChEBI CHEBI:3374
ChEMBL Ligand CHEMBL294199
DrugCentral Ligand 3064
GtoPdb PubChem SID 53801090
PubChem CID 1548943
RCSB PDB Ligand 4DY
Search Google for chemical match using the InChIKey YKPUWZUDDOIDPM-SOFGYWHQSA-N
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Search PubMed clinical trials capsaicin
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Search UniChem for chemical match using the InChIKey YKPUWZUDDOIDPM-SOFGYWHQSA-N
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Wikipedia Capsaicin

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Tocris
(E)-Capsaicin
Cat. No. 0462