Entacapone - Moligand™, ≥98% , Catechol O-methyltransferase inhibitor, CAS No.130929-57-6, Catechol O-methyltransferase inhibitor

CAS: 130929-57-6 Cat. No.: E125270 Peso molecular: 305.29 Número EC: 603-449-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

(2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide | 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide | (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Descripción general

Entacapone inhibits catechol-O-methyltransferase(COMT) with IC50 of 151 nM.
A peripherally acting inhibitor of catechol-O-methyl transferase.

Entacapone has been used in high-performance bioaffinity chromatography.

Specifications

Sinónimos

(2E)-2-Cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-N, N-diethyl-2-propenamide | 2-Cyano-N, N-diethyl-3-(3, 4-dihydroxy-5-nitrophenyl)propenamide | (E)-2-cyano-3-(3, 4-dihydroxy-5-nitrophenyl)-N, N-diethylacrylamide

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Potent catecholO-methyltransferase (COMT) inhibitor (IC50values are 14.3, 20.1 and 73.3 nM for rat liver soluble COMT, total COMT and membrane-bound COMT respectively). Increases bioavailability of levodopa when given as an adjunct therapy for Parkinson's

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Argon charged

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Catechol O-methyltransferase inhibitor

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488195229
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195229
• Sonrisas canónicas: CCN(CC)C(=O)C(=CC1=CC(=C(C(=C1)O)O)[N+](=O)[O-])C#N
• IUPAC Name: (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
• InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N
• 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+
• Isómeros SMILES: CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N
• WGK Alemania: 3
• CAS alternativo: 116314-67-1
• Peso molecular: 305.29
• Reaxy-Rn: 14523938
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14523938&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxycinnamic acids and derivatives
• Alternative Parents: Nitrophenols Nitrobenzenes Nitroaromatic compounds Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Tertiary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Nitriles Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• 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
• Descripción: This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
• External Descriptors: monocarboxylic acid amide - catechols - nitrile

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

MPC2 Tbio Mitochondrial pyruvate carrier 2 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MPC1L Tdark Mitochondrial pyruvate carrier 1-like protein (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

COMT Tclin Catechol O-methyltransferase (5 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

COMT Tclin Catechol O-methyltransferase (404 Activities)

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Homo sapiens (32628 Activities)

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HepG2 (196354 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT2B15 Tbio UDP-glucuronosyltransferase 2B15 (172 Activities)

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PDXK Tbio Pyridoxal kinase (263 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UGT1A8 Tbio UDP-glucuronosyltransferase 1-8 (233 Activities)

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UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)

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KYAT3 Tbio Kynurenine--oxoglutarate transaminase 3 (9 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTO Tchem Alpha-ketoglutarate-dependent dioxygenase FTO (473 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADI1 Tbio 1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase (4 Activities)

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GCDH Tbio Glutaryl-CoA dehydrogenase, mitochondrial (8 Activities)

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NIPSNAP3A Tdark Protein NipSnap homolog 3A (3 Activities)

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HIBCH Tbio 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial (11 Activities)

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Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Brain (1 Activities)

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Plasma (328 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Solvent:DMSO, Max Conc. mg/mL: 30.53, Max Conc. mM: 100; Solvent:ethanol, Max Conc. mg/mL: 3.05, Max Conc. mM: 10
• Sensibilidad: Air sensitive，Heat sensitive
• Punto de fusión (°C): 162 °C
• Peso molecular: 305.290 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 305.101 Da
• Monoisotopic Mass: 305.101 Da
• Topological Polar Surface Area: 130.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 500.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Referencias

1. Liangliang Zhu, Hui Lv, Ling Xiao, Yanyao Hou, Wenjuan Li, Guangbo Ge, Chunzhi Ai.  (2022)  Diverse effects of α-/β-estradiol on catalytic activities of human UDP-glucuronosyltransferases (UGT).  JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY,      [PMID:36181991] [10.1016/j.jsbmb.2022.106196]

2. X. Cui, Y. Zhou, Y. Zheng, L. Cao, L. Gao, J. Duan, H. Yin, S. Ai.  (2022)  Investigation of the enhanced photoactivity of CdS/Bi2MoO6/MoSe2 and its application in antibody-free enzyme-assisted photoelectrochemical strategy for detection of N6-methyladenosine and FTO protein.  Materials Today Nano,      [PMID:] [10.1016/j.mtnano.2022.100269]

3. Ling Xiao, Dehui Chi, Guiju Sheng, Wenjuan Li, Penghui Lin, Sicheng Liang, Liangliang Zhu, Peipei Dong.  (2020)  Inhibitory effects of UDP-glucuronosyltransferase (UGT) typical ligands against E. coli beta-glucuronidase (GUS).  RSC Advances,  10  (39): (22966-22971).  [PMID:35520305] [10.1039/D0RA02311F]

4. Xia Lv, Xin-Xin Wang, Jie Hou, Zhong-Ze Fang, Jing-Jing Wu, Yun-Feng Cao, Shu-Wen Liu, Guang-Bo Ge, Ling Yang.  (2016)  Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:27089846] [10.1016/j.taap.2016.04.009]