ophiobolin C
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Grundinformationen
- CAS
19022-51-6- Standard-SMILES
CC(C)=CCCC(C)[C@H]1CC[C@]2(C)C[C@H]3[C@H](C(=O)C[C@]3(C)O)/C(C=O)=C\C[C@@H]12- InChIKey
PLWMYIADTRHIMY-BNFAVABNSA-N- Summenformel
- C25H38O3
- Durchschnittliche Molmasse
- 386,57 g/mol
Namen und Bezeichner
- Bevorzugter Name
- ophiobolin C
- Englischer Name
- ophiobolin C
- Summenformel
- C25H38O3
- Molmasse
- 386.57
Namen und Synonyme
Zizanin Aophiobolin C3-Hydroxy-5-oxoophiobola-7,19-dien-25-alDicyclopenta[a,d]cyclooctene-4-carboxaldehyde, 7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1-hydroxy-1,9a-dimethyl-3-oxo-, (1R,3aS,6aS,7R,9aR,10aS)-
Datenbank-Bezeichner
- CAS
19022-51-6- PubChem CID
- 6440957
Eigenschaften
Physikochemische Eigenschaften
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- Aggregatzustand
- A solid
Chemie und Industrie
Anwendungen
BeschreibungOphiobolin C is a sesterterpenoid fungal phytoxin produced by many species of the genus Bipolaris. It has been identified as an antagonist of chemokine receptor CCR5 binding (IC50 = 40 μM) to the envelope protein gp120 and to CD4, which is known to mediate HIV-1 viral entry into cells. Ophiobolin C is also reported to be cytotoxic to chronic lymphocytic leukemia cells (LC50 = 8 nM).
VerwendenOphiobolin C is a member of the ophiobolin class of phytotoxic metabolites produced by many species of the genus Bipolaris. Ophiobolin C inhibits human CCR5 binding to the envelope protein gp120 and CD4 that mediates HIV-1 entry into cells. Blockade of this binding was considered by scientists at Merck as a potential new mode of action for the treatment of HIV-1 infection.
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