Decursinol angelate - ≥98% , CAS No.130848-06-5

CAS: 130848-06-5 Cat. No.: D413068 Molecular Weight: 328.36 EC Number: 111-881-7

GRADE & PURITY ≥98%

Synonyms

DTXSID401315533 | Decursinolangelate | MS-24919 | E80810 | HY-N4322 | [(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate | UNII-LXU5241LCL | (S)-8,8-dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-7-yl (Z)-2-meth

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Decursinol angelate Decursinol angelate is a cytotoxic and protein kinase C activating agent from the root of Angelica gigas.

Targets

PKC

In vitro

Decursinol angelate (DA) blocks PGE2-induced activation of the EP2 receptor signaling pathway, including the activation of PKA and the phosphorylation of CREB. Decursinol angelate also inhibits PGE2-induced expression of cyclooxygenase-2 and the activation of the Ras/Raf/Erk pathway, which activates downstream targets for cell survival. Decursinol angelate greatly reduces the PGE2-induced activation of NF-κB p50 and p65 subunits. It has been reported to suppress the growth of estrogen-stimulated and estrogen-independent growth and survival of breast cancer MCF-7 and MDA-MB-231 cells. Decursinol angelate also suppresses the growth of cancer cells through the inhibition of phosphatidylinositol 3\'-kinase (PI3K)/Akt, extracellular-signal-regulated kinase (Erk) and nuclear factor-κB (NFκB). Decursinol angelate has anti-leukemic activity through the suppression of protein kinase C activation in human leukemia cells.

In vivo

Decursinol angelate has anti-angiogenic activity both in vitro and in vivo.

Cell Research(from reference)

Cell lines：MCF-7 cells 

Concentrations：10 μM, 20 μM, 50 μM 

Incubation Time：24 hours 

Specifications

Synonyms

DTXSID401315533 | Decursinolangelate | MS-24919 | E80810 | HY-N4322 | [(3S)-2, 2-dimethyl-8-oxo-3, 4-dihydropyrano[3, 2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate | UNII-LXU5241LCL | (S)-8, 8-dimethyl-2-oxo-7, 8-dihydro-2H, 6H-pyrano[3, 2-g]chromen-7-yl (Z)-2-meth

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Decursinol angelate is a cytotoxic and protein kinase C activating agent from the root of Angelica gigas.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Product Properties

• ALogP: 3.955
• hba_count: 5
• Rotatable Bond: 3

Names and Identifiers

• Pubchem Sid: 504760135
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760135
• Canonical Smiles: CC=C(C)C(=O)OC1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C
• IUPAC Name: [(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate
• InChIKey: AGABNGOXUSXQDD-XKGFZTIGSA-N
• INCHI: 1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/b11-5-/t16-/m0/s1
• Isomeric SMILES: C/C=C(/C)\C(=O)O[C@H]1CC2=C(C=C3C(=C2)C=CC(=O)O3)OC1(C)C
• Molecular Weight: 328.36
• Reaxy-Rn: 1435897
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1435897&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Pyranocoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Pyranocoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: Linear pyranocoumarins
• Alternative Parents: Pyranochromenes 2,2-dimethyl-1-benzopyrans Pyranones and derivatives Fatty acid esters Alkyl aryl ethers Benzenoids Heteroaromatic compounds Enoate esters Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Linear pyranocoumarin - Pyranochromene - 2,2-dimethyl-1-benzopyran - Chromane - Benzopyran - 1-benzopyran - Alkyl aryl ether - Pyranone - Fatty acid ester - Pyran - Fatty acyl - Benzenoid - Heteroaromatic compound - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Lactone - Carboxylic acid ester - Carboxylic acid derivative - Oxacycle - Ether - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.
• 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)

B16 (5829 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 65 mg/mL (197.95 mM)
• Sensitivity: Light sensitive
• DMSO(mg / mL) Max Solubility: 65
• DMSO(mM) Max Solubility: 197.9534657
• Molecular Weight: 328.400 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 328.131 Da
• Monoisotopic Mass: 328.131 Da
• Topological Polar Surface Area: 61.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 589.000
• 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