CHEBI:66522 - stevastelin B

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ChEBI Name stevastelin B
ChEBI ID CHEBI:66522
Definition A 15-membered cyclodepsipeptide isolated from the culture broth of Penicillium sp. It exhibits significant immunosuppressive effect on T-cell activiation.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H61N3O9
Net Charge 0
Average Mass 655.86280
Monoisotopic Mass 655.441
InChI InChI=1S/C34H61N3O9/c1-8-9-10-11-12-13-14-15-16-17-18-19-27-22(4)30(40)23(5)31(41)36-28(21(2)3)32(42)37-29(24(6)38)33(43)35-26(34(44)46-27)20-45-25(7)39/h21-24,26-30,38,40H,8-20H2,1-7H3,(H,35,43)(H,36,41)(H,37,42)/t22-,23+,24+,26-,27+,28-,29-,30+/m0/s1
InChIKey UTYDHKYGSNIIDV-RFYOCORYSA-N
SMILES CCCCCCCCCCCCC[C@H]1OC(=O)[C@H](COC(C)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C)[C@H](O)[C@H]1C)C(C)C)[C@@H](C)O
Metabolite of Species Details
Penicillium (NCBI:txid5073) of strain NK374186 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(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.
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
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 stevastelin B (CHEBI:66522) has role Penicillium metabolite (CHEBI:76964)
stevastelin B (CHEBI:66522) has role immunosuppressive agent (CHEBI:35705)
stevastelin B (CHEBI:66522) is a cyclodepsipeptide (CHEBI:35213)
stevastelin B (CHEBI:66522) is a macrocycle (CHEBI:51026)
IUPAC Name
[(3S,9S,12R,13R,14R,15R)-13-hydroxy-6-(1-hydroxyethyl)-12,14-dimethyl-2,5,8,11-tetraoxo-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecan-3-yl]methyl acetate
Registry Number Type Source
7631162 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12109115 PubMed citation Europe PMC
16277304 PubMed citation Europe PMC
8002401 PubMed citation Europe PMC
8698640 PubMed citation Europe PMC
8698641 PubMed citation Europe PMC
9195865 PubMed citation Europe PMC
Last Modified
13 January 2014