Isochromophilone V

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Category Enzyme inhibitors
Catalog number BBF-01511
CAS 167355-56-8
Molecular Weight 350.84
Molecular Formula C19H23ClO4
Purity >98%

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Description

Isochromophilone III is produced by the strain of Pen. multicolor FO-3216 and FO-2328. It inhibited the ACAT of rat hepatocellular microsome and the B-16 melanoma cell with the IC50 (μmol/L) of 50 and 36.

Specification

Synonyms 6H-2-Benzopyran-6-one, 5-chloro-3-(3,5-dimethyl-1,3-heptadienyl)-7,8-dihydro-7,8-dihydroxy-7-methyl
IUPAC Name (7R,8R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7,8-dihydroxy-7-methyl-8H-isochromen-6-one
Canonical SMILES CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C(C(C2=CO1)O)(C)O)Cl
InChI InChI=1S/C19H23ClO4/c1-5-11(2)8-12(3)6-7-13-9-14-15(10-24-13)17(21)19(4,23)18(22)16(14)20/h6-11,17,21,23H,5H2,1-4H3/b7-6+,12-8+/t11-,17+,19+/m0/s1
InChI Key ZFOBGKZKFOAYTR-ZZSXOZOGSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 492.4°C at 760 mmHg
Melting Point 58-61°C
Density 1.25 g/cm3

Reference Reading

1. Isochromophilones III-VI, inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium multicolor FO-3216
N Arai, K Shiomi, H Tomoda, N Tabata, D J Yang, R Masuma, T Kawakubo, S Omura J Antibiot (Tokyo). 1995 Jul;48(7):696-702. doi: 10.7164/antibiotics.48.696.
New azaphilones named isochromophilones III-VI were isolated from the culture broth of Penicillium multicolor FO-3216 as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). Their structures were elucidated by NMR and other spectroscopic analyses. The IC50 values of isochromophilones III, IV, V and VI for ACAT activity in an enzyme assay using rat liver microsomes were calculated to be 110, 50, 50 and 120 microM, respectively.

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