You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:20 UTC
Update Date2017-10-23 19:06:01 UTC
HMDB IDHMDB0012226
Secondary Accession Numbers
  • HMDB12226
Metabolite Identification
Common NameEntacapone
DescriptionEntacapone is an inhibitor drug of catechol O-methyltransferase, which catalyzes the reaction between catechol and S-adenosyl-L-methionine to produce guaiacol and S-adenosyl-L-homocysteine.
Structure
Thumb
Synonyms
ValueSource
(e)-alpha-cyano-N,N-Diethyl-3,4-dihydroxy-5-nitrocinnamamideChEBI
ComtanChEBI
ComtessChEBI
EntacaponaChEBI
EntacaponumChEBI
N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamideChEBI
(e)-a-cyano-N,N-Diethyl-3,4-dihydroxy-5-nitrocinnamamideGenerator
(e)-α-cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamideGenerator
2-cyano-N,N-Diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamideHMDB
Orion brand OF entacaponeMeSH
Novartis brand OF entacaponeMeSH
Chemical FormulaC14H15N3O5
Average Molecular Weight305.286
Monoisotopic Molecular Weight305.101170605
IUPAC Name(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
Traditional Nameentacapone
CAS Registry Number130929-57-6
SMILES
CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N
InChI Identifier
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 KeyJRURYQJSLYLRLN-BJMVGYQFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Hydroxycinnamic acid or derivatives
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • C-nitro compound
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carbonitrile
  • Nitrile
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    General disorders and administration site conditions:

    Vascular disorders:

    Psychiatric disorders:

Disposition

Route of exposure:

  Enteral:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP2.5ALOGPS
logP1.63ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)5.68ChemAxon
pKa (Strongest Basic)-0.036ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area130.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.51 m³·mol⁻¹ChemAxon
Polarizability29.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-4190000000-da6b28638ec4920bd58aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0059-6004900000-14645ab585cbbed0ca38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0329000000-8d20a5650e9c1b1c8275View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0329000000-8d20a5650e9c1b1c8275View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-6e08b463d5af43617517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-1069000000-5075a6f93c2b72c3483aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-9240000000-27e088a40b83e29661e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-29c32f9a04e379fce5feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2009000000-6d53b89d8a9ecd3b180eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-5f330d3ad8cb0af17a9aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028870
KNApSAcK IDNot Available
Chemspider ID4444537
KEGG Compound IDC07943
BioCyc IDCPD-7662
BiGG IDNot Available
Wikipedia LinkEntacapone
METLIN IDNot Available
PubChem Compound5281081
PDB IDNot Available
ChEBI ID4798
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Valkovic P, Benetin J, Blazicek P, Valkovicova L, Gmitterova K, Kukumberg P: Reduced plasma homocysteine levels in levodopa/entacapone treated Parkinson patients. Parkinsonism Relat Disord. 2005 Jun;11(4):253-6. Epub 2005 Apr 20. [PubMed:15878587 ]
  2. Durif F, Devaux I, Pere JJ, Delumeau JC, Bourdeix I: Efficacy and tolerability of entacapone as adjunctive therapy to levodopa in patients with Parkinson's disease and end-of-dose deterioration in daily medical practice: an open, multicenter study. Eur Neurol. 2001;45(2):111-8. [PubMed:11244274 ]
  3. Factor SA, Molho ES, Feustel PJ, Brown DL, Evans SM: Long-term comparative experience with tolcapone and entacapone in advanced Parkinson's disease. Clin Neuropharmacol. 2001 Sep-Oct;24(5):295-9. [PubMed:11586115 ]
  4. Leppanen J, Savolainen J, Nevalainen T, Forsberg M, Huuskonen J, Taipale H, Gynther J, Mannisto PT, Jarvinen T: Synthesis and in-vitro/in-vivo evaluation of orally administered entacapone prodrugs. J Pharm Pharmacol. 2001 Nov;53(11):1489-98. [PubMed:11732751 ]
  5. Authors unspecified: Entacapone/levodopa/carbidopa combination tablet: Stalevo. Drugs R D. 2003;4(5):310-1. [PubMed:12952501 ]
  6. Authors unspecified: Levodopa + carbidopa + entacapone. Entacapone: a second look: new preparations. Parkinson's disease: a modest effect. Prescrire Int. 2005 Apr;14(76):51-4. [PubMed:15875340 ]
  7. Gottwald MD: Entacapone, a catechol-O-methyltransferase inhibitor for treating Parkinson's disease: review and current status. Expert Opin Investig Drugs. 1999 Apr;8(4):453-62. [PubMed:15992091 ]
  8. Kinnings SL, Liu N, Buchmeier N, Tonge PJ, Xie L, Bourne PE: Drug discovery using chemical systems biology: repositioning the safe medicine Comtan to treat multi-drug and extensively drug resistant tuberculosis. PLoS Comput Biol. 2009 Jul;5(7):e1000423. doi: 10.1371/journal.pcbi.1000423. Epub 2009 Jul 3. [PubMed:19578428 ]
  9. Hamaue N, Ogata A, Terado M, Tsuchida S, Yabe I, Sasaki H, Hirafuji M, Togashi H, Aoki T: Entacapone, a catechol-O-methyltransferase inhibitor, improves the motor activity and dopamine content of basal ganglia in a rat model of Parkinson's disease induced by Japanese encephalitis virus. Brain Res. 2010 Jan 14;1309:110-5. doi: 10.1016/j.brainres.2009.10.055. Epub 2009 Oct 29. [PubMed:19879254 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495