CHEBI:29582 - ascomycin

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ChEBI Name ascomycin
ChEBI ID CHEBI:29582
Definition A macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C43H69NO12
Net Charge 0
Average Mass 792.00750
Monoisotopic Mass 791.48198
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-NURRSENYSA-N
SMILES CC[C@@H]1\C=C(C)\C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@H](C)C[C@@H]2OC)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@@H]([C@H](C)[C@@H](O)CC1=O)C(\C)=C\[C@@H]1CC[C@@H](O)[C@@H](C1)OC
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ascomycin (CHEBI:29582) has role antifungal agent (CHEBI:35718)
ascomycin (CHEBI:29582) has role bacterial metabolite (CHEBI:76969)
ascomycin (CHEBI:29582) has role immunosuppressive agent (CHEBI:35705)
ascomycin (CHEBI:29582) is a ether (CHEBI:25698)
ascomycin (CHEBI:29582) is a lactol (CHEBI:38131)
ascomycin (CHEBI:29582) is a macrolide (CHEBI:25106)
ascomycin (CHEBI:29582) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
Synonyms Sources
FK 520 ChemIDplus
FK520 KEGG COMPOUND
FR 900520 ChemIDplus
Immunomycin KEGG COMPOUND
L 683590 ChemIDplus
Manual Xrefs Databases
Ascomycin Wikipedia
C00017631 KNApSAcK
C12102 KEGG COMPOUND
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Registry Numbers Types Sources
104987-12-4 CAS Registry Number KEGG COMPOUND
104987-12-4 CAS Registry Number ChemIDplus
5372600 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21833838 PubMed citation Europe PMC
23435975 PubMed citation Europe PMC
24628911 PubMed citation Europe PMC
3198493 PubMed citation Europe PMC
7520900 PubMed citation Europe PMC
Last Modified
15 July 2015