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CHEBI:66523 - stevastelin B3

ChEBI IDCHEBI:66523
ChEBI Namestevastelin B3
Stars
DefinitionA 13-membered cyclodepsipeptide isolated from the culture broth of Penicillium sp. It exhibits significant immunosuppressive effect on T-cell activiation.
Last Modified13 January 2014
DownloadsMolfile
FormulaC34H61N3O9
Net Charge0
Average Mass655.874
Monoisotopic Mass655.44078
SMILESCCCCCCCCCCCCC[C@@H](O)[C@H](C)[C@H]1OC(=O)[C@H](COC(C)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1C
InChIInChI=1S/C34H61N3O9/c1-8-9-10-11-12-13-14-15-16-17-18-19-27(40)22(4)30-23(5)31(41)36-28(21(2)3)32(42)37-29(24(6)38)33(43)35-26(34(44)46-30)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
InChIKeyNVCZDYLTENUTNV-RFYOCORYSA-N
Species of MetaboliteComponentSourceComments
Penicillium (ncbitaxon:5073) - PubMed (8002401) Strain: NK374186
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
stevastelin B3 (CHEBI:66523) has role Penicillium metabolite (CHEBI:76964)
stevastelin B3 (CHEBI:66523) has role immunosuppressive agent (CHEBI:35705)
stevastelin B3 (CHEBI:66523) is a cyclodepsipeptide (CHEBI:35213)
stevastelin B3 (CHEBI:66523) is a macrocycle (CHEBI:51026)
IUPAC Name 
[(3S,6S,9S,12R,13R)-6-(1-hydroxyethyl)-13-[(2S,3R)-3-hydroxyhexadecan-2-yl]-12-methyl-2,5,8,11-tetraoxo-9-(propan-2-yl)-1-oxa-4,7,10-triazacyclotridecan-3-yl]methyl acetate
Registry NumbersSources
Reaxys:9979425Reaxys
Citations