Isochromophilone III
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01509 |
| CAS | 167173-89-9 |
| Molecular Weight | 352.85 |
| Molecular Formula | C19H25ClO4 |
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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 110 and 33.
Specification
| Synonyms | 6H-2-Benzopyran-6-one, 5-chloro-3-(3,5-dimethyl-1,3-heptadienyl)-1,7,8,8a-tetrahydro-7,8-dihydroxy-7-methyl |
| IUPAC Name | (7R,8R,8aR)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7,8-dihydroxy-7-methyl-8,8a-dihydro-1H-isochromen-6-one |
| Canonical SMILES | CCC(C)C=C(C)C=CC1=CC2=C(C(=O)C(C(C2CO1)O)(C)O)Cl |
| InChI | InChI=1S/C19H25ClO4/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/h6-9,11,15,17,21,23H,5,10H2,1-4H3/b7-6+,12-8+/t11-,15-,17+,19+/m0/s1 |
| InChI Key | GJRRBURMULHWIH-WPHCLLNESA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 489.1°C at 760 mmHg |
| Melting Point | 84-85°C |
| Density | 1.22 g/cm3 |
Reference Reading
1. Azaphilones with endothelin receptor binding activity produced by Penicillium sclerotiorum: taxonomy, fermentation, isolation, structure elucidation and biological activity
L Pairet, S K Wrigley, I Chetland, E E Reynolds, M A Hayes, J Holloway, A M Ainsworth, W Katzer, X M Cheng, D J Hupe, et al. J Antibiot (Tokyo). 1995 Sep;48(9):913-23. doi: 10.7164/antibiotics.48.913.
A series of azaphilones produced by Penicillium sclerotiorum (Xenova culture collection number X11853) active in assays for the detection of antagonists of the endothelin-A (ETA) and endothelin-B (ETB) receptors has been identified. The series includes two novel sclerotiorin analogues, (8S,8 alpha-R)-7-deacetyl-1,O8,8,8a-tetrahydro-7-epi-sclerotiorin, 1, and its 5-dechloro analogue, 2. It also includes 5-chloroisorotiorin, 6, previously unreported as a natural product, in addition to the major product of these fermentations, (+)-sclerotiorin, 5. Data for the inhibition of endothelin-1 (ET-1) and endothelin-3 (ET-3) binding in the ETA and ETB receptor assays respectively are reported for this series. Compounds 1 and 2 were more selective for the rabbit ETA receptor than for the rat ETB receptor. The IC50 values for 1 and 2 were 9 and 28 microM respectively in an assay based on binding of ET-1 to rabbit ETA receptors. In an assay based on the binding of ET-3 to the rat ETB receptor compounds 1 and 2 exhibited IC50's of 77 and 172 microM. Members of this series of compounds demonstrated antagonist behavior in a secondary assay based on blockade of ET-1 stimulated arachidonic acid release from rabbit renal artery smooth muscle cells, when present at concentrations of > or = 30 microM.
2. 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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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 ╳
