ChemicalBook > CAS DataBase List > OPHIOBOLIN A

OPHIOBOLIN A

Product Name: OPHIOBOLIN A
CAS No.: 4611-05-6
Chemical Name: OPHIOBOLIN A
Synonyms: ophiobolin;cochliobolin;OPHIOBOLIN A;COCHLIOBOLIN A;Ophiobolin A >=95% (HPLC);Ophiobolin A (Cochliobolin A);Ophiobolin, Helminthosporium sp.;Cochliobolin A, Ophiobolin, Ophiobalin;ophiobolin A from helminthosporium sp.;18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
CBNumber: CB2735485
Molecular Formula: C25H36O4
Formula Weight: 400.55
MOL File: 4611-05-6.mol

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OPHIOBOLIN A Property

Melting point:: 182°C
Boiling point:: 443.19°C (rough estimate)
Density: 1.0278 (rough estimate)
refractive index: 1.4460 (estimate)
storage temp.: 2-8°C
solubility: Soluble in DMSO (up to 10 mg/ml)
form: White to off-white solid.
pka: 13.84±0.70(Predicted)
color: White
biological source: (from Biopolaris leersia fungal metabolite)
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22
Safety Statements: 36
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: RL1576000
HS Code: 2932190090
Toxicity: mouse,LD50,intraperitoneal,21mg/kg (21mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 143, 1981.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1478
Product name: Ophiobolin A
Purity: ≥95% (HPLC)
Packaging: 100μG
Price: $91.67
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1478
Product name: Ophiobolin A
Purity: ≥95% (HPLC)
Packaging: 1MG
Price: $378
Updated: 2025/07/31

Cayman Chemical

Product number: 15381
Product name: Ophiobolin A
Purity: ≥95%
Packaging: 1mg
Price: $275
Updated: 2024/03/01

Cayman Chemical

Product number: 15381
Product name: Ophiobolin A
Purity: ≥95%
Packaging: 5mg
Price: $820
Updated: 2024/03/01

Usbiological

Product number: 207314
Product name: Ophiobolin A
Packaging: 100ug
Price: $312
Updated: 2021/12/16

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OPHIOBOLIN A Chemical Properties,Usage,Production

Description

Ophiobolin A (4611-05-6) selectively inhibits the growth of cancer cells (IC50=0.4-4.3 μM) over normal cells (IC50=20.9 μM).1 Induces non-apoptotic cell death in glioblastoma cells and is active in an in vivo model.2 Covalently reacts with primary amines such as lysine side chains2 and phosphatidylethanolamine3 forming unique pyrrole adducts. Induces ER stress4, paraptosis4 and autophagy5.

Uses

Ophiobolin A is the dominant member of a class of phytotoxic metabolites produced by plant pathogenic fungi. Ophiobolin A acts by inhibiting calmodulin action in calcium regulation.

Definition

ChEBI: A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18.

References

[1] DIMPLE R. BHATIA . Anticancer activity of Ophiobolin A, isolated from the endophytic fungus Bipolaris setariae[J]. Natural Product Research, 2016, 30 12: Pages 1455-1458. DOI:10.1080/14786419.2015.1062760
[2] RAMESH DASARI . Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure–activity relationship and unique pyrrolylation of primary amines[J]. Bioorganic & Medicinal Chemistry Letters, 2015, 25 20: Pages 4544-4548. DOI:10.1016/j.bmcl.2015.08.066
[3] CHRISTOPHER CHIDLEY. The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine.[J]. eLife, 2016. DOI:10.7554/elife.14601
[4] IN YOUNG KIM. Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostasis.[J]. Oncotarget, 2017, 8 63: 106740-106752. DOI:10.18632/oncotarget.22537
[5] C. RODOLFO. Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells[J]. PLoS ONE, 2016, 11 1. DOI:10.1371/journal.pone.0167672

OPHIOBOLIN A Preparation Products And Raw materials

Raw materials

Preparation Products

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OPHIOBOLIN A Suppliers

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4611-05-6, OPHIOBOLIN ARelated Search:

(R)-(-)-1-OCTEN-3-OL, 99 Diacetone Alcohol 2-Isopropyl-5-methyl-2-hexenal 7-METHOXY-3,7-DIMETHYLOCTANAL ALLYLCYCLOPENTANE CYCLOOCTENE OPHIOBOLIN A 2,2-DIMETHYLTETRAHYDROFURAN 3-METHYLCYCLOOCTENE 1-METHYL-1-CYCLOOCTENE undec-1-en-3-ol 2-PROPYL-2-HEPTENAL OPHIOBOLIN H ophiobolin C 2,4-DIMETHYLCYCLOPENTANONE OPHIOBOLIN B Ophiobolin methoxy bromide ophiobolin M

18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14

cochliobolin

ophiobolin

COCHLIOBOLIN A

ophiobolin A from helminthosporium sp.

Ophiobolin, Helminthosporium sp.

(18R)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

(18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-diene-25-al

Cochliobolin A, Ophiobolin, Ophiobalin

OPHIOBOLIN A

Spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxo-, (2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-

Ophiobolin A >=95% (HPLC)

Ophiobolin A (Cochliobolin A)

4611-05-6

C25H36O4

Cell Signaling and Neuroscience

Calcium Antagonists

Cell Biology

BioChemical

Intracellular Calcium Signaling