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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:20 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012226
Secondary Accession Numbers
  • HMDB12226
Metabolite Identification
Common NameEntacapone
DescriptionEntacapone, also known as comtan or comtess, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Entacapone is a drug which is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic parkinson's disease who experience the signs and symptoms of end-of-dose "wearing-off". Based on a literature review a significant number of articles have been published on Entacapone.
Structure
Data?1582753029
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 entacaponeHMDB
Novartis brand OF entacaponeHMDB
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
Description Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic 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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+165.24330932474
DeepCCS[M-H]-161.41630932474
DeepCCS[M-2H]-197.76430932474
DeepCCS[M+Na]+173.80930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EntacaponeCCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N3690.9Standard polar33892256
EntacaponeCCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N2334.1Standard non polar33892256
EntacaponeCCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N2629.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Entacapone,1TMS,isomer #1CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C12708.9Semi standard non polar33892256
Entacapone,1TMS,isomer #2CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O)C([N+](=O)[O-])=C12731.5Semi standard non polar33892256
Entacapone,2TMS,isomer #1CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C12752.1Semi standard non polar33892256
Entacapone,1TBDMS,isomer #1CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C12947.4Semi standard non polar33892256
Entacapone,1TBDMS,isomer #2CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C([N+](=O)[O-])=C12966.0Semi standard non polar33892256
Entacapone,2TBDMS,isomer #1CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C13157.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Entacapone GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-4190000000-da6b28638ec4920bd58a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Entacapone GC-MS (2 TMS) - 70eV, Positivesplash10-0059-6004900000-14645ab585cbbed0ca382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Entacapone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Entacapone LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0329000000-8d20a5650e9c1b1c82752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Entacapone , positive-QTOFsplash10-0a4i-0329000000-8d20a5650e9c1b1c82752017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOFsplash10-0a4i-0009000000-6e08b463d5af436175172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOFsplash10-0udr-1069000000-5075a6f93c2b72c3483a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOFsplash10-0fkc-9240000000-27e088a40b83e29661e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOFsplash10-0udi-0009000000-29c32f9a04e379fce5fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOFsplash10-0udi-2009000000-6d53b89d8a9ecd3b180e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOFsplash10-00dl-9100000000-5f330d3ad8cb0af17a9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOFsplash10-0a4i-0009000000-62e9f24f62db1840e2e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOFsplash10-001i-1292000000-28b9a09056bdc465cd192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOFsplash10-0a4i-1590000000-58fe447bc05aa84201882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOFsplash10-0udi-0039000000-85f49c3b07fd9b1dd7bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOFsplash10-0pb9-1693000000-bf7093c3dc0b31a75e5d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOFsplash10-0a4j-5910000000-658aee735015de149a672021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00494
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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