Ophiobolin B

Base Information

• Chemical Name: Ophiobolin B
• CAS No.: 5601-74-1
• Molecular Formula: C25H38O4
• Molecular Weight: 402.57
• Hs Code.: 2932190090
• ChEMBL ID: CHEMBL478388
• Metabolomics Workbench ID: 137762
• Nikkaji Number: J14.568H
• Wikidata: Q105263286
• Mol file: 5601-74-1.mol

Synonyms:Ophiobolin B;5601-74-1;3,14-Dihydroxy-5-oxoophiobola-7,19-dien-25-al;Ophiobola-7,19-dien-25-al, 3,14-dihydroxy-5-oxo-;(1R,3S,4R,7S,8E,11R,12S)-4,12-dihydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde;CHEMBL478388;SCHEMBL15542271;HY-N6780;AKOS040733918;CS-0042378

Chemical Property of Ophiobolin B

Chemical Property:

• PSA: 74.60000
• LogP: 4.39160
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 402.27700969
• Heavy Atom Count: 29
• Complexity: 733

Purity/Quality:

99% ^*data from raw suppliers

Ophiobolin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1(CCC2(C1CC=C(C3C(C2)C(CC3=O)(C)O)C=O)C)O
• Isomeric SMILES: C[C@@H](CCC=C(C)C)[C@]1(CC[C@]2([C@H]1C/C=C(\[C@@H]3[C@H](C2)[C@](CC3=O)(C)O)/C=O)C)O
• Uses: Ophiobolin B is a minor member of a class of phytotoxic metabolites produced by Bipolaris and other genera of plant pathogenic fungi. Ophiobolin B acts by inhibiting calmodulin action in calcium regulation. Calmodulin is a calcium-sensing protein that regulates a wide array of proteins involved in diverse cellular functions. Ophiobolin B is a sesterterpenoid fungal phytotoxin that binds and irreversibly antagonizes calmodulin, producing cytotoxic and antimicrobial effects. It induces apoptosis in chronic lymphocytic leukemia cells with an LC50 value of 2 nM and in different zygomycetes with MIC values ranging from 25-50 μg/ml.[Cayman Chemical] Ophiobolin B is a fungal phytotoxin and inhibits calmodulin (a protein involved in calcium regulation). Ophiobolin B also exhibit antibacterial and antitumor activities.

Technology Process of Ophiobolin B

There total 2 articles about Ophiobolin B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ Zizanin B (5601-74-1,19184-64-6)

Guidance literature:

Tetraol IVa, CrO3;

Reference yield:

→ Zizanin (5601-74-1,19184-64-6)

Guidance literature:

Helminthosphorium Zazaniae;