Kavain (+/-) - 10mM in DMSO , CAS No.500-64-1

CAS: 500-64-1 Cat. No.: K424312 Molecular Weight: 230.3 Beilstein Registry Number: 177877

GRADE & PURITY 10mM in DMSO

Synonyms

(R)-(+)-Kavain | Kavaform (TN) | (6R)-4-methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one | (+)-Kavain | DTXCID3013595 | kavaine | CHEBI:92164 | Tox21_200907 | DTXSID5033595 | HMS2095J15 | AC-35093 | KAWAIN [MI] | 2H-Pyran-2-one,6-dihydro-4-methoxy

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Kavain (+/-), a lipophilic kavapyrone, has been originally extracted from|Piper methysticum|. This compound has been shown to significantly antagonize dopamine depletion in murine striatal neurons. Additional studies report that Kavain (+/-) impairs vascular smooth muscle contraction via inhibition of Ca|+|channels, causing relaxation in precontracted murine ileum, airways, and aortic rings. Furthermore, at high concentrations, this agent has been noted to display neurotoxic characteristics.

Specifications

Synonyms

(R)-(+)-Kavain | Kavaform (TN) | (6R)-4-methoxy-6-[(E)-2-phenylvinyl]-5, 6-dihydro-2H-pyran-2-one | (+)-Kavain | DTXCID3013595 | kavaine | CHEBI:92164 | Tox21_200907 | DTXSID5033595 | HMS2095J15 | AC-35093 | KAWAIN [MI] | 2H-Pyran-2-one, 6-dihydro-4-methoxy

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: COC1=CC(=O)OC(C1)C=CC2=CC=CC=C2
• IUPAC Name: (2R)-4-methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
• InChIKey: XEAQIWGXBXCYFX-GUOLPTJISA-N
• INCHI: 1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
• Isomeric SMILES: COC1=CC(=O)O[C@H](C1)/C=C/C2=CC=CC=C2
• WGK Germany: 3
• RTECS: UQ0518000
• Molecular Weight: 230.3
• Beilstein: 177877
• Reaxy-Rn: 84886
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=84886&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Kavalactones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Kavalactones
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Kavalactones
• Alternative Parents: Styrenes Dihydropyranones Vinylogous esters Enoate esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Kavalactone - Styrene - Dihydropyranone - Monocyclic benzene moiety - Pyran - Benzenoid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Vinylogous ester - Lactone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.
• External Descriptors: Polyketides - alpha-Pyrones

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

Associated Targets(Human)

RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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GMNN Tbio Geminin (128009 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Echinochloa crus-galli (3685 Activities)

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Fusarium solani (1274 Activities)

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Plasmodium falciparum (966862 Activities)

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Fusarium oxysporum (3998 Activities)

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Trichoderma viride (1263 Activities)

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PC-12 (7051 Activities)

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Lactuca sativa (1092 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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PA Polymerase acidic protein (806 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: n20D1.57
• Boil Point(°C): 432.64° C at 760 mmHg (Predicted)
• Melt Point(°C): 105.5° C
• Molecular Weight: 230.260 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094 Da
• Monoisotopic Mass: 230.094 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 324.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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