Amidepsine D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00672 |
| CAS | 79786-34-8 |
| Molecular Weight | 496.46 |
| Molecular Formula | C26H24O10 |
| Purity | ≥95% |
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Description
It is produced by the strain of Humicola sp. FO-2942. It inhibits DGAT activity, and the IC50 of rat liver microsomes DGAT is 17.5 X 10-6 mol/L. It also inhibits triacylglycerol formation in intact Raji cells.
Specification
| Synonyms | 2,4-di-O-methylgyrophoric acid; 4-[(2,4-Dimethoxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methyl-Benzoic Acid 4-Carboxy-3-hydroxy-5-methylphenyl Ester |
| Storage | Store at -20°C |
| IUPAC Name | 4-[4-(2,4-dimethoxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoyl]oxy-2-hydroxy-6-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)O)O)OC(=O)C2=C(C=C(C=C2C)OC(=O)C3=C(C=C(C=C3C)OC)OC)O |
| InChI | InChI=1S/C26H24O10/c1-12-7-16(9-18(27)21(12)24(29)30)35-25(31)22-13(2)8-17(10-19(22)28)36-26(32)23-14(3)6-15(33-4)11-20(23)34-5/h6-11,27-28H,1-5H3,(H,29,30) |
| InChI Key | KODVVMZOLYYCMV-UHFFFAOYSA-N |
Properties
| Appearance | White to Light Pink Solid |
| Antibiotic Activity Spectrum | Mycobacteria |
| Boiling Point | 701.3±60.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Ethanol |
Reference Reading
1. New monordens produced by amidepsine-producing fungus Humicola sp. FO-2942
Ichiji Namatame, Masayoshi Arai, Kazunobu Yamamoto, Hiroshi Tomoda, Satoshi Omura J Antibiot (Tokyo) . 2003 Jun;56(6):526-32. doi: 10.7164/antibiotics.56.526.
Based on UV spectrum-guided purification, new monordens C, D and E, known monordens A (radicicol) and B and 5-O-methylsclerone were isolated from the fermentation broth of amidepsine-producing Humicola sp. FO-2942 by solvent extraction, silica-gel column chromatography, ODS column chromatography and HPLC. All monordens cause the cell cycle arrest at G1 and G2/M phases in Jurkat cells. But among them, monordens A and E show antifungal activity only against Aspergillus niger.
2. Structure elucidation of new monordens produced by Humicola sp. FO-2942
Hiroko Hatano, Masayoshi Arai, Kazunobu Yamamoto, Hiroshi Tomoda, Kazuro Shiomi, Satoshi Omura J Antibiot (Tokyo) . 2003 Jun;56(6):533-8. doi: 10.7164/antibiotics.56.533.
Structures of three novel compounds designated monordens C to E, isolated from the fermentation broth of amidepsine-producing fungus Humicola sp. FO-2942, were elucidated by spectroscopic evidence. Monordens C is 6,7-dihydromonorden A. Monordens D and E lack the epoxide moiety of monordens C and B, respectively.
3. Amidepsines, inhibitors of diacylglycerol acyltransferase produced by Humicola sp. FO-2942. II. Structure elucidation of amidepsines A, B and C
N Tabata, S Omura, H Tomoda, M Ito J Antibiot (Tokyo) . 1995 Sep;48(9):942-7. doi: 10.7164/antibiotics.48.942.
Structures of amidepsines A, B, C and D, diacylglycerol acyltransferase (DGAT) inhibitors, were determined by spectroscopic studies including various NMR measurements. They were elucidated as 2-hydroxy-4-[[2-hydroxy-4-[(2,4-dimethoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]-oxy]-6-methylbenzoic acid N-alanine amide for amidepsine A, 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid N-alanine amide for amidepsine B and 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid N-valine amide for amidepsine C. Amidepsine D was identified with 2,4-di-O-methylgryphoric acid.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
