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577-64-0

577-64-0 Structure

577-64-0 Structure
IdentificationBack Directory
[Name]

asterric acid
[CAS]

577-64-0
[Synonyms]

asterric acid
DiMethylosoic acid,TAN 1415A, WF 12880A
2-(2-Methoxycarbonyl-4-hydroxy-6-methoxyphenoxy)-4-methyl-6-hydroxybenzoic acid
Benzoic acid, 2-(2-carboxy-3-hydroxy-5-methylphenoxy)-5-hydroxy-3-methoxy-, 1-methyl ester
[Molecular Formula]

C17H16O8
[MDL Number]

MFCD00216131
[MOL File]

577-64-0.mol
[Molecular Weight]

348.3
Chemical PropertiesBack Directory
[Melting point ]

208-214 °C
[Boiling point ]

557.6±50.0 °C(Predicted)
[density ]

1.406±0.06 g/cm3(Predicted)
[storage temp. ]

?20°C
[solubility ]

Soluble in ethanol;Soluble in DMSO;Soluble in dimethyl formamide
[form ]

solid
[pka]

2.97±0.34(Predicted)
[color ]

white
[Major Application]

metabolomics
vitamins, nutraceuticals, and natural products
[InChI]

1S/C17H16O8/c1-8-4-11(19)14(16(20)21)12(5-8)25-15-10(17(22)24-3)6-9(18)7-13(15)23-2/h4-7,18-19H,1-3H3,(H,20,21)
[InChIKey]

XOKVHFNTYHPEHN-UHFFFAOYSA-N
[SMILES]

O(C)c1c(c(cc(c1)O)C(=O)OC)Oc2c(c(cc(c2)C)O)C(=O)O
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

50
[Safety Statements ]

61
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
Hazard InformationBack Directory
[Uses]

Asterric acid is a fungal metabolite with anti-angiogenic properties, isolated from a number of Aspergillus and Penicillium species. It is an inhibitor of vascular endothelial growth factor (VEGF), inhibiting VEGF-induced tube formation of human umbilical vein endothelial cells.
[Biological Activity]

asterric acid is an eta receptor inhibitor.endothelin (et), a potent vasoconstrictor/pressor peptide consisting of 21 amino acid residues, was first isolated from the cultures of porcine aortic endothelial cells. analyses of a human genomic library reveals three forms of et (et-1, et-2 and et-3) with more than 70% homology with one another. in various organs, high affinity and specific receptors for et have been found, which have been classfied as receptors eta and etb. et-1 has potent and long-lasting vasoconstrictive activity, as a result of binding to the eta receptor.
[in vitro]

previous study asterric acid isolated as an active substance from the culture filtrate of a fungus, aspergillus sp. asterric acid had also been reported as a metabolite of a fungus. it was found that asterric acid had the property of inhibiting et-1 binding to the eta receptor of a10 cells, but it showed no inhibitory activity against anp and a ii binding at 10 mm, which indicated that asterric acid displayed as a specific inhibitor of et-1 binding [1].
[IC 50]

10 μm for et-1 binding to the eta receptor ofa10 cells
[References]

[1] ohashi, h. ,akiyama, h.,nishikori, k., et al. asterric acid, a new endothelin binding inhibitor. journal of antibiotics 45, 1684-1685 (1992).
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