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CHEBI:66523 - stevastelin B3

Default Structure
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:
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:
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