Basic information
- CAS
4611-05-6- Standard SMILES
CC(C)=CC1CC(C)C2(CCC3(C)CC4C(C(=O)CC4(C)O)/C(C=O)=C\CC32)O1- InChIKey
MWYYLZRWWNBROW-FMQZQXMHSA-N- Molecular formula
- C25H36O4
- Average molar mass
- 400.5 g/mol
- Monoisotopic mass
- 400.26135963
Names & identifiers
- Preferred name
- Cochliobolin A
- IUPAC
- (8'E)-4'-hydroxy-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradec-8-ene]-8'-carbaldehyde
- English name
- OPHIOBOLIN A
- Molecular formula
- C25H36O4
- Molecular weight
- 400.55
Names & synonyms
Cochliobolin ANSC114340CHEMBL1967869Ophiobola-7, 14,18-epoxy-3-hydroxy-5-oxo-, (18R)-ophiobolincochliobolinOPHIOBOLIN AOphiobolin A >=95% (HPLC)Ophiobolin A (Cochliobolin A)Ophiobolin, Helminthosporium sp.Cochliobolin A, Ophiobolin, Ophiobalinophiobolin A from helminthosporium sp.
Show more names
18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
Database identifiers
- CAS
4611-05-6- PubChem CID
- 5352017
- ChEMBL
CHEMBL1967869
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 778
Physicochemical properties
- Melting point
- 182 °C · 182°C
- Boiling point
- 443.19 °C · 443.19°C (rough estimate)
- Density
- 1.0278 · 1.0278 (rough estimate)
- refractive index
- 1.446 · 1.4460 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO (up to 10 mg/ml)
- form
- White to off-white solid.
- pka
- 13.84 · 13.84±0.70(Predicted)
- color
- White
- biological source
- (from Biopolaris leersia fungal metabolite)
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
- InChIKey
- MWYYLZRWWNBROW-BDZRSQQBSA-N
- SMILES
- [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
- UNSPSC Code
- 12352200 · 12352200
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- RL1576000
- ridadr
- UN 2811 6.1/PG 3
- 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.
- risk_code
- 20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Applications
DescriptionOphiobolin 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.
UsesOphiobolin 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.
Suppliers23 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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