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Merck
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文件

A3835

Sigma-Aldrich

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

greener alternative

同義詞:

Changchuanmycin, FK-520, FR900520, Immunomycin, L 683590

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About This Item

經驗公式(希爾表示法):
C43H69NO12
CAS號碼:
分子量::
792.01
MDL號碼:
分類程式碼代碼:
12352200
PubChem物質ID:
NACRES:
NA.77

形狀

powder

品質等級

環保替代產品評分

old score: 59
new score: 54
Find out more about DOZN™ Scoring

環保替代產品特色

Designing Safer Chemicals
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

抗生素活性譜

fungi

環保替代類別

作用方式

enzyme | inhibits

儲存溫度

−20°C

SMILES 字串

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 密鑰

ZDQSOHOQTUFQEM-NURRSENYSA-N

一般說明

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
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Designing Safer Chemicals” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

生化/生理作用

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.

聯結

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

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


分析證明 (COA)

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Engineering of the LysR family transcriptional regulator FkbR1 and its target gene to improve ascomycin production
Song K, et al.
Applied Microbiology and Biotechnology, 101(11), 4581-4592 (2017)
Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation.
K W Mollison et al.
Annals of the New York Academy of Sciences, 685, 55-57 (1993-06-23)
Discovery of Less Nephrotoxic FK506 Analogs and Determining Immunophilin Dependence of Immunosuppressant Nephrotoxicity with a Novel Single-Dose Rat Cisplatin Potentiation Assay
Mollison KW, et al.
Journal of Pharmacology and Experimental Therapeutics, 283(3), 1509-1519 (1997)
Jingjing Xie et al.
Journal of medicinal chemistry, 52(11), 3516-3522 (2009-05-09)
We developed an in-cell NMR assay for screening small molecule interactor libraries (SMILI-NMR) for compounds capable of disrupting or enhancing specific interactions between two or more components of a biomolecular complex. The method relies on the formation of a well-defined
Patrizia Ferraboschi et al.
The Journal of antibiotics, 65(7), 349-354 (2012-04-19)
Tacrolimus is an immunosuppressant macrolactam of fermentative origin. By means of HPLC, LC-MS and NMR analyses, coupled with the reference standard synthesis, the main impurities of tacrolimus bulk drug samples were identified and their chemical-physical properties reported. Known ascomycin and

文章

提供用於免疫系統信號靶點鑑定/驗證以及抗生素、抗病毒藥物和抗真菌藥物的生物活性小分子。

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

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