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CHEBI:64531 - fumitremorgin B

Default Structure
ChEBI IDCHEBI:64531
ChEBI Namefumitremorgin B
Stars
DefinitionAn organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi via a tryptophan-proline diketopiperazine intermediate.
Last Modified25 March 2013
SubmitterSteve
DownloadsMolfile
FormulaC27H33N3O5
Net Charge0
Average Mass479.577
Monoisotopic Mass479.24202
SMILES[H][C@@]12CCCN1C(=O)[C@]1(O)[C@@H](O)c3c(n(CC=C(C)C)c4cc(OC)ccc34)[C@]([H])(C=C(C)C)N1C2=O
InChIInChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1
InChIKeyWEIYXEFMCIRZHC-MWGWWEMPSA-N
Roles Classification
Biological Roles:
mycotoxin  Poisonous substance produced by fungi.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
fumitremorgin B (CHEBI:64531) has role mycotoxin (CHEBI:25442)
fumitremorgin B (CHEBI:64531) is a indole alkaloid (CHEBI:38958)
fumitremorgin B (CHEBI:64531) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name 
(5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
Synonym  Source
LanosulinChemIDplus
UniProt Name  Source
fumitremorgin BUniProt
Registry NumbersSources
Reaxys:905336Reaxys
CAS:12626-17-4ChemIDplus
Citations