entacapone   Click here for help

GtoPdb Ligand ID: 6647

Synonyms: Comtan® | Comtess® | OR-611
Approved drug PDB Ligand
entacapone is an approved drug (FDA (1999), EMA (1998))
Compound class: Synthetic organic
Comment: Entacapone inhibits catechol O-methyltransferase (COMT).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 127.7
Molecular weight 305.1
XLogP 2.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCN(C(=O)C(=Cc1cc(O)c(c(c1)[N+](=O)[O-])O)C#N)CC
Isomeric SMILES CCN(C(=O)/C(=C/c1cc(O)c(c(c1)[N+](=O)[O-])O)/C#N)CC
InChI InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
InChI Key JRURYQJSLYLRLN-BJMVGYQFSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Catechol-O-methyltransferase Primary target of this compound Hs Inhibitor Inhibition 8.7 – 9.5 pKi - 1
pKi 9.5 (Ki 3x10-10 M) soluble enzyme [1]
Description: soluble enzyme
pKi 8.7 (Ki 2x10-9 M) membrane-bound enzyme [1]
Description: membrane-bound enzyme