Ascomycin

Ascomycin, produced by the fermentation of S. hygroscopicus subsp. ascomyceticus, is an ethyl analog of tacrolimus (FK-506) with potent immunosuppressant properties that prevents T-cell proliferation through initial binding to FK-506-binding protein 12 (FKBP12), an immunophilin that acts as the principal mediator of FK506- and rapamycin-induced immunosuppression. Ascomycin inhibits the enzymatic peptidyl-prolyl cis-trans isomerase and chaperone activities of PfFKBP35, an FKBP from P. falciparum, a causative agent of malaria in humans with an IC50 value of 0.52 µM.Formal Name: (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone. CAS Number: 104987-12-4. Synonyms: Changchuanmycin, FK-520, FR900520, Immunomycin, L 683590. Molecular Formula: C43H69NO12. Formula Weight: 792.0. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml, DMSO: 30 mg/ml, Ethanol: 20 mg/ml. SMILES: O=C(C(N1[C@H](C(O[C@@H]([C@@H]([C@@H](O)CC([C@H](CC)/C=C(C[C@H](C)C[C@@H]2OC)\C)=O)C)/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)=O)CCCC1)=O)[C@]4(O)O[C@H]2[C@@H](OC)C[C@H]4C. InChi Code: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24. InChi Key: ZDQSOHOQTUFQEM-NURRSENYSA-N.