Phomopsin A

Phomopsins are a family of mycotoxins produced by the fungus D. toxica, which predominantly infects lupines. Ingestion of lupines infected with D. toxica causes lupinosis, a degenerative disorder that can result in acute liver damage, brain damage, and death. Phomopsin A is a cyclic hexapeptide mycotoxin that binds beta-tubulin in a vinca domain, overlapping with the site targeted by vinblastine (Cay-11762) and other tubulin inhibitors. It binds beta-tubulin from higher organisms but not alpha-tubulin or fungal mycelial tubulin. Phomopsin A blocks microtubule growth, modulates the dynamics of microtubules, and interferes with mitosis.Formal Name: (2E)-(betaS)-3-chloro-beta,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-(2E)-2,3-didehydroisoleucyl-2,3-didehydro-aspartic acid, cyclic (15->3)-ether. CAS Number: 64925-80-0. Synonyms: NSC 381839. Molecular Formula: C36H45ClN6O12. Formula Weight: 789.2. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. SMILES: OC(/C(NC(/C(NC([C@H]1N(C([C@@H]2NC([C@H](C(C)=C)NC([C@@H](NC)[C@H](C3=CC(O[C@@]2(CC)C)=C(O)C(Cl)=C3)O)=O)=O)=O)CC=C1)=O)=C(CC)/C)=O)=C\C(O)=O)=O. InChi Code: InChI=1S/C36H45ClN6O12/c1-8-17(5)25(32(50)39-20(35(53)54)15-23(44)45)41-30(48)21-11-10-12-43(21)34(52)29-36(6,9-2)55-22-14-18(13-19(37)28(22)47)27(46)26(38-7)33(51)40-24(16(3)4)31(49)42-29/h10-11,13-15,21,24,26-27,29,38,46-47H,3,8-9,12H2,1-2,4-7H3,(H. InChi Key: FAFRRYBYQKPKSY-MSBSFVTFSA-N.