Cyclocurcumin , CAS No.153127-42-5

CAS: 153127-42-5 Cat. No.: C650574 Molecular Weight: 368.38 PubChem CID: 69879809

Synonyms

HY-N8251 | BDBM50501397 | AKOS040761556 | LS-14853 | (E)-2-(4-hydroxy-3-methoxyphenyl)-6-(4-hydroxy-3-methoxystyryl)-2H-pyran-4(3H)-one | SCHEMBL23040676 | 4H-Pyran-4-one,2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-6-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Cyclocurcumin is a potent p38α inhibitor. Cyclocurcumin shows antirheumatic, antivasoconstrictive and antioxidant activities .

In Vitro

Cyclocurcumin (10-40 μM; 18 h) leads to significant inhibition in the release of TNF-α in a dose-dependent manner in LPS-stimulated human macrophages. Cyclocurcumin (5-25 μM) inhibits phenylephrine -induced vasocontraction in a concentration-dependent manner (IC 50 =14.9±1.0 μM) in freshly isolated rat aortic rings. Cyclocurcumin (5-25 μM; 30 min) inhibits influx of intracellular calcium in a dose-dependent manner. Cyclocurcumin inhibits L-type calcium channel-mediated vasoconstriction in a concentration-dependent manner. The anticontractile effect of Cyclocurcumin is reversible. Cyclocurcumin has strong activity as a scavenger of ˙OH and ˙OOH free radicals preferentially by its 4′-OH phenolic radical via a hydrogen-atom transfer mechanism in water and a physiological environment. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Specifications

Synonyms

HY-N8251 | BDBM50501397 | AKOS040761556 | LS-14853 | (E)-2-(4-hydroxy-3-methoxyphenyl)-6-(4-hydroxy-3-methoxystyryl)-2H-pyran-4(3H)-one | SCHEMBL23040676 | 4H-Pyran-4-one, 2, 3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-6-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen

Biochemical and Physiological Mechanisms

Cyclocurcumin is a potent p38α inhibitor. Cyclocurcumin shows antirheumatic, antivasoconstrictive and antioxidant activities.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: COC1=C(C=CC(=C1)C=CC2=CC(=O)CC(O2)C3=CC(=C(C=C3)O)OC)O
• IUPAC Name: 2-(4-hydroxy-3-methoxyphenyl)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2,3-dihydropyran-4-one
• InChIKey: IZLBLUIBVMGMIY-ZZXKWVIFSA-N
• INCHI: 1S/C21H20O6/c1-25-20-9-13(4-7-17(20)23)3-6-16-11-15(22)12-19(27-16)14-5-8-18(24)21(10-14)26-2/h3-11,19,23-24H,12H2,1-2H3/b6-3+
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C2=CC(=O)CC(O2)C3=CC(=C(C=C3)O)OC)O
• Alternate CAS: 153127-42-5
• PubChem CID: 69879809
• MeSH Entry Terms: 2-(4-hydroxy-3-methoxyphenyl)-6-((E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl)-2,3-dihydropyran-4-one;cyclocurcumin
• Molecular Weight: 368.38

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Diarylheptanoids
      • Subclass Linear diarylheptanoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Diarylheptanoids
• Subclass: Linear diarylheptanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Linear diarylheptanoids
• Alternative Parents: Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Dihydropyranones Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Vinylogous esters Cyclic ketones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Linear 1,7-diphenylheptane skeleton - Methoxyphenol - Phenoxy compound - Anisole - Phenol ether - Styrene - Methoxybenzene - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Dihydropyranone - Phenol - Monocyclic benzene moiety - Benzenoid - Vinylogous ester - Ketone - Cyclic ketone - Oxacycle - Ether - Organoheterocyclic compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
• External Descriptors: Not available

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(non-human)

Aorta (2975 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 368.400 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 368.126 Da
• Monoisotopic Mass: 368.126 Da
• Topological Polar Surface Area: 85.200 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 571.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1