A3835

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

• Synonym(s): Changchuanmycin, FK-520, FR900520, Immunomycin, L 683590
• Empirical Formula (Hill Notation): C₄₃H₆₉NO₁₂
• CAS Number: 104987-12-4
• Molecular Weight: 792.01
• MDL number: MFCD06198665
• UNSPSC Code: 12352200
• PubChem Substance ID: 24890817
• NACRES: NA.77

Properties

• form: powder
• Quality Level: 200
• greener alternative product score: old score: 59; new score: 54; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Designing Safer Chemicals; Design for Energy Efficiency; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• antibiotic activity spectrum: fungi
• greener alternative category: , Re-engineered
• mode of action: enzyme | inhibits
• storage temp.: −20°C
• SMILES string: CCC1\C=C(C)\C[C@H](C)C[C@H](OC)C2O[C@](O)([C@H](C)C[C@@H]2OC)C(=O)C(=O)N3CCCC[C@H]3C(=O)OC([C@H](C)[C@@H](O)CC1=O)\C(C)=C\[C@@H]4CC[C@@H](O)[C@@H](C4)OC
• 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
• InChI key: ZDQSOHOQTUFQEM-NURRSENYSA-N

Description

General description

Ascomycin (FK520) is a macrolide and macrolactone antibiotic isolated from the soil bacterium, Streptomyces hygroscopicus var. ascomyceticus. Ascomycin is a C21 ethyl analog of the macrolide tacrolimus (FK-506). It is a 23-membered polyketide macrolide.

Chemical structure: macrolactam

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Biochem/physiol Actions

Ascomycin is a strong immunosuppressant. It inhibits allogenic T-lymphocyte proliferation and can bind with high affinity to FKBP and inhibits calcineurin phosphatase in the nM range.

Ascomycin (FK520) possesses high anti-fungal and immunosuppressant activity. Ascomycin has been shown to inhibit the peptidyl-prolyl cis-trans isomerase activity of FK-506-binding proteins of T cells.

Linkage

An FK506 analog with an ethyl rather than an allyl group at position 21.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves