(+)-Ophiobolin A

Names

[ Name ]:
(+)-Ophiobolin A

[Synonym ]:
COCHLIOBOLIN A
(18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-diene-25-al
18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
Ophiobolin A
cochliobolin
ophiobolin
Ophiobolin,Helminthosporium sp.
orphiobolin A
(7E,18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al
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-, (3S,3'S,3aR,5E,5'R,6aS,9R,9aS,10aR)-
(18R)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

Biological Activity

[Description]:

Ophiobolin A, a fungal metabolite and a phytotoxin, is a potent and irreversibly inhibitor of calmodulin-activated cyclic nucleotide phosphodiesterase, with an IC50 value of 9 μM. Ophiobolin A antimicrobial and anticancer activity[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Infection

[Target]

IC50: 9 μM (calmodulin-activated cyclic nucleotide phosphodiesterase)[1].

[References]

[1]. Leung PC, et al. Ophiobolin A. A natural product inhibitor of calmodulin. J Biol Chem. 1984 Mar 10;259(5):2742-7

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
539.4±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₃₆O₄

[ Molecular Weight ]:
400.551

[ Flash Point ]:
177.8±23.6 °C

[ Exact Mass ]:
400.261353

[ PSA ]:
63.60000

[ LogP ]:
3.75

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.554

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RL1576000

CHEMICAL NAME :: Ophiobola-7,19-dien-25-al, 14,18-epoxy-3-hydroxy-5-oxo-, (18R)-

CAS REGISTRY NUMBER :: 4611-05-6

LAST UPDATED :: 198211

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C25-H36-O4

MOLECULAR WEIGHT :: 400.61

WISWESSER LINE NOTATION :: L C585 FV LX HUTJ A1 DQ D1 HVH L-& BT5OXTJ C1 E1UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 238 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,143,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 21 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,143,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 73 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,143,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,143,1981

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H312 + H332

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P261-P280

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
UN 2811 6.1/PG 3

[ RTECS ]:
RL1576000