CHEBI:207346 - (−)-FR901483

ChEBI IDCHEBI:207346
ChEBI Name(−)-FR901483
Stars
ASCII Name(-)-FR901483
DefinitionAn organic heterotricyclic compound that is 2-(methylamino)octahydro-1H-7,10a-methanopyrrolo[1,2-a]azocin-6-ol substituted by 4-methoxybenzyl and phosphonooxy groups at positions 5 and 8, respectively (the 2S,5S,6S,7R,8S,10aS-stereoisomer). It is an immunosuppressant isolated from the fermentation broth of Cladobotryum sp. 11231.
Last Modified28 January 2025
SubmitterMetaboLights
DownloadsMolfile
FormulaC20H31N2O6P
Net Charge0
Average Mass426.450
Monoisotopic Mass426.19197
SMILES[H][C@]12C[C@@]3(CC[C@@H]1OP(=O)(O)O)C[C@H](NC)CN3[C@@H](Cc1ccc(OC)cc1)[C@H]2O
InChIInChI=1S/C20H31N2O6P/c1-21-14-10-20-8-7-18(28-29(24,25)26)16(11-20)19(23)17(22(20)12-14)9-13-3-5-15(27-2)6-4-13/h3-6,14,16-19,21,23H,7-12H2,1-2H3,(H2,24,25,26)/t14-,16-,17-,18-,19-,20+/m0/s1
InChIKeyCIISYBZFZSWZLX-KKMIJOEASA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cladobotryum sp. (ncbitaxon:2040732) - PubMed (8609083) Strain: 11231
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.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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)
(−)-FR901483 (CHEBI:207346) has role fungal metabolite (CHEBI:76946)
(−)-FR901483 (CHEBI:207346) has role immunosuppressive agent (CHEBI:35705)
(−)-FR901483 (CHEBI:207346) is a monomethoxybenzene (CHEBI:25235)
(−)-FR901483 (CHEBI:207346) is a organic heterotricyclic compound (CHEBI:26979)
(−)-FR901483 (CHEBI:207346) is a organic phosphate (CHEBI:25703)
(−)-FR901483 (CHEBI:207346) is a secondary alcohol (CHEBI:35681)
(−)-FR901483 (CHEBI:207346) is a secondary amino compound (CHEBI:50995)
(−)-FR901483 (CHEBI:207346) is conjugate acid of (−)-FR901483(2−) (CHEBI:233173)
Incoming Relation(s)
(−)-FR901483(2−) (CHEBI:233173) is conjugate base of (−)-FR901483 (CHEBI:207346)
IUPAC Name 
(2S,5S,6S,7R,8S,10aS)-6-hydroxy-5-(4-methoxybenzyl)-2-(methylamino)octahydro-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dihydrogen phosphate
Synonyms  Source
FR 901483ChEBI
FR-901483ChEBI
FR901483ChEBI
Manual XrefsDatabases
8085979ChemSpider
C00016174KNApSAcK
FR901483Wikipedia
Citations