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SML1478 Sigma-Aldrich

Ophiobolin A

≥95% (HPLC)

Synonym: (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

  • CAS Number 4611-05-6

  • Empirical Formula (Hill Notation) C25H36O4

  • Molecular Weight 400.55

  •  PubChem Substance ID 329825909

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Intracellular Calcium Regulators,
Quality Level   100
biological source   (from Biopolaris leersia fungal metabolite)
assay   ≥95% (HPLC)
form   powder
storage condition   protect from light
color   white to beige
storage temp.   −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
InChI key   MWYYLZRWWNBROW-BDZRSQQBSA-N

Description

Packaging

1 mg in glass bottle

Biochem/physiol Actions

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.

Other Notes

Light and air sensitive.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
RL1576000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
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