capsaicin   Click here for help

GtoPdb Ligand ID: 2486

Synonyms: Qutenza®
Approved drug PDB Ligand
capsaicin is an approved drug (EMA & FDA (2009))
Compound class: Natural product
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.
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2D Structure
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Physico-chemical Properties
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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Natural product
Approved drug? Yes (EMA & FDA (2009))
Approved drug? Yes. FDA (2009)  |  EMA (2009)
IUPAC Name Click here for help
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
International Nonproprietary Names Click here for help
INN number INN
10145 capsaicin
Synonyms Click here for help
Qutenza®
Database Links Click here for help
BindingDB Ligand 20461
CAS Registry No. 404-86-4
ChEBI CHEBI:3374
ChEMBL Ligand CHEMBL294199
DrugCentral Ligand 3064
GtoPdb PubChem SID 53801090
LIPID MAPS LMFA08020085
PubChem CID 1548943
RCSB PDB Ligand 4DY
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UniChem Compound Search for chemical match using the InChIKey YKPUWZUDDOIDPM-SOFGYWHQSA-N
UniChem Connectivity Search for chemical match using the InChIKey YKPUWZUDDOIDPM-SOFGYWHQSA-N
Wikipedia Capsaicin

Product suppliers

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MedChemExpress
Capsaicin (links to external site)
Cat. No. HY-10448
Capsaicin (Purity 65%) (links to external site)
Cat. No. HY-10448A
Capsaicin (Standard) (links to external site)
Cat. No. HY-10448R