Fleephilone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00941 |
| CAS | 183239-76-1 |
| Molecular Weight | 441.47 |
| Molecular Formula | C24H27NO7 |
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Description
Fleephilone is an antibiotic produced by Trichoderma harzianum. It has the combination of inhibiting viral particle regulation (REV) protein and [33P] labeled viral particle regulatory response element (RRE) RNA, with IC50 of 7.6 mol/L.
Specification
| Synonyms | (2aR,3S,10cR)-3-hydroxy-8-methyl-7,9-dioxo-1-[(1E,3E)-penta-1,3-dien-1-yl]-2a,4,5,8,9,10c-hexahydro-3H,7H-2-oxa-5a-azaaceanthrylen-8-yl 3-hydroxybutanoate |
| IUPAC Name | [(12S,13R,16R)-12-hydroxy-5-methyl-4,6-dioxo-15-[(1E,3E)-penta-1,3-dienyl]-14-oxa-9-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,7-trien-5-yl] 3-hydroxybutanoate |
| Canonical SMILES | CC=CC=CC1=C2C3C(O1)C(CCN3C=C4C2=CC(=O)C(C4=O)(C)OC(=O)CC(C)O)O |
| InChI | InChI=1S/C24H27NO7/c1-4-5-6-7-17-20-14-11-18(28)24(3,32-19(29)10-13(2)26)23(30)15(14)12-25-9-8-16(27)22(31-17)21(20)25/h4-7,11-13,16,21-22,26-27H,8-10H2,1-3H3/b5-4+,7-6+/t13?,16-,21+,22-,24?/m0/s1 |
| InChI Key | UOPRBHLVKJBASE-XVSBCJMYSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | viruses |
| Boiling Point | 707.6°C at 760 mmHg |
| Density | 1.35 g/cm3 |
Reference Reading
1. Harziphilone and fleephilone, two new HIV REV/RRE binding inhibitors produced by Trichoderma harzianum
J Qian-Cutrone, S Huang, L P Chang, D M Pirnik, S E Klohr, R A Dalterio, R Hugill, S Lowe, M Alam, K F Kadow J Antibiot (Tokyo). 1996 Oct;49(10):990-7. doi: 10.7164/antibiotics.49.990.
During the screening of the natural products for their ability to inhibit the binding of REV (regulation of virion expression) protein to [33P] labeled RRE (REV responsive element) RNA, two novel fungal metabolites, harziphilone and fleephilone, were isolated from the butanol-methanol (1:1) extract of the fermentation broth of Trichoderma harzianum by bioassay guided fractionation. The structures of these two new compounds were established by spectroscopic methods. Harziphilone and fleephilone showed inhibitory activity against the binding of REV-protein to RRE RNA with IC50 values of 2.0 microM and 7.6 microM, respectively. However both compounds did not protect CEM-SS cells from acute HIV infection at concentration levels up to 200 micrograms/ml using an XTT dye reduction assay. In addition, harziphilone demonstrated cytotoxicity at 38 microM against the murine tumor cell line M-109.
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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 ╳
