| Identification | Back 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 Properties | Back 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 Data | Back 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 Information | Back 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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