Ascomycin, Calcineurin/PP2B inhibitor

Key facts

CAS number

104987-12-4

Purity

>98%

Form

Solid

form

Source

Streptomyces hygroscopicus var. ascomyceticus

Molecular weight

792 Da

Molecular formula

C₄₃H₆₉NO₁₂

PubChem

6437370

Nature

Native

Solubility

Soluble in DMSO to 50 mM

Soluble in ethanol to 100 mM

Biochemical name

Ascomycin(FK 520)

Biological description

Calcineurin/PP2B inhibitor (IC₅₀ = 49 nM). Forms a FK-506 binding protein 12 (FKBP12) - Ascomycin -Calcineurin complex. Immunosuppressant and antifungal activity in vitro and in vivo.

Canonical smiles

CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C

Isomeric smiles

CC[C@@H]1/C=C(\C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC)C)/C

InChi

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/b24-18-,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1

InChiKey

ZDQSOHOQTUFQEM-PKUCKEGBSA-N

IUPAC Name

(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone