SML1478

Ophiobolin A

≥95% (HPLC)

• Synonym(e): (2′S,3′S,3aR,5′R,6aS,9R,9aS,10aR)-1,3a,4,4′,5′,6a,7,8,9,9a,10,10a-Dodecahydro-9-hydroxy-3′,9,10a-trimethyl-5′-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2′(3′H)-furan]-6-carboxaldehyde
• Empirische Formel (Hill-System): C₂₅H₃₆O₄
• CAS-Nummer: 4611-05-6
• Molekulargewicht: 400.55
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 329825909
• NACRES: NA.77

Eigenschaften

• Biologische Quelle: (from Biopolaris leersia fungal metabolite)
• Qualitätsniveau: 100
• Assay: ≥95% (HPLC)
• Form: powder
• Lagerbedingungen: protect from light
• Farbe: white to beige
• Lagertemp.: −20°C
• SMILES String: [H]C(/C1=C/C[C@]([C@]2(O[C@@H](C=C(C)C)C[C@@H]2C)CC3)([H])[C@@]3(C)C[C@@]([C@](C)(O)C4)([H])[C@]1([H])C4=O)=O
• InChI: 1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1
• InChIKey: MWYYLZRWWNBROW-BDZRSQQBSA-N

Beschreibung

Biochem./physiol. Wirkung

Ophiobolin A is a fungal metabolite, toxic to many crops and found to have antimicrobial and anticancer activity. Ophiobolin A is a calmodulin antagonist and inhibitor of big conductance Ca2+-activated K+ channel (BKCa) activity. Its anticancer activity may involve inhibition of multiple oncogenic signaling pathways including PI3K/mTOR, Ras/Raf/ERK and CDK/RB. One study suggested the possibility of pyrrolylation of lysine residues on its intracellular target protein(s) as a mechanism of action on various targets.

Sonstige Hinweise

Light and air sensitive.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301
• P-Sätze: P264 - P270 - P301 + P310 - P405 - P501
• Gefahreneinstufungen: Acute Tox. 3 Oral
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable