5-Bromoochrephilone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00184 |
| CAS | |
| Molecular Weight | 461.34 |
| Molecular Formula | C23H25BrO5 |
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Description
5-Bromoochrephilone is one of the products of Penicillum multicolor FO-2338 in broth containing potassium bromide. It has strong inhibitory activity on gP120-CD4 binding.
Specification
| IUPAC Name | (6aR,9R,9aR)-9-acetyl-5-bromo-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-6a-methyl-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione |
| Canonical SMILES | CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C3(C(C2=CO1)C(C(=O)O3)C(=O)C)C)Br |
| InChI | InChI=1S/C23H25BrO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12,18-19H,6H2,1-5H3/b8-7+,13-9+/t12-,18-,19-,23+/m0/s1 |
| InChI Key | YVLXPVGJCIVWMQ-WJKJBVSTSA-N |
Reference Reading
1. New brominated and halogen-less derivatives and structure-activity relationship of azaphilones inhibiting gp120-CD4 binding
K Matsuzaki, H Tahara, J Inokoshi, H Tanaka, R Masuma, S Omura J Antibiot (Tokyo). 1998 Nov;51(11):1004-11. doi: 10.7164/antibiotics.51.1004.
Novel brominated and halogen-less azaphilone (oxoisochromane) derivatives, 5-bromoochrephilone and dechloroisochromophilone IV, and known derivatives, dechloroisochromophilone III and isorotiorin, were isolated from the culture broth of a producing organism of isochromophilones I and II (azaphilones inhibiting gp120-CD4 binding), Penicillium multicolor FO-2338, fermented in a medium containing potassium bromide. Nineteen azaphilone-related compounds isolated from the above strain and from other fungi were tested for the inhibition of gp120-CD4 binding and the structure-activity relationship is discussed. Consequently, 5-bromoochrephilone is the strongest inhibitor (IC50, 2.5 microM). A halogen atom at C-5, a proton at C-8 and a diene structure in C-3 side chain of 6-oxoisochromane ring are necessary for gp120-CD4 binding.
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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 ╳
