A potent macrolide immunosuppressant
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Ascomycin

Item No. 11309

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 30 mg/mlEthanol: 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    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.1,2 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.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mrowietz, U. Macrolide immunosuppressants. Eur. J. Dermatol. 9(5), 346-351 (1999).

    2. Andexer, J.N., Kendrew, S.G., Nur-e-Alam, M., et al. Biosynthesis of the immunosuppressants FK506, FK520, and rapamycin involves a previously undescribed family of enzymes acting on chorismate. Proc. Natl. Acad. Sci. USA 108(12), 4776-4781 (2011).

    3. Monaghan, P., Fardis, M., Revill, W.P., et al. Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds. J. Infect. Dis. 191(8), 1342-1349 (2005).