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:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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)
(−)-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
FR901483ChEBI
FR-901483ChEBI
FR 901483ChEBI
Manual XrefsDatabases
8085979ChemSpider
C00016174KNApSAcK
FR901483Wikipedia
Citations