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CHEBI:65724 - 9-deacetoxyfumigaclavine C

ChEBI IDCHEBI:65724
ChEBI Name9-deacetoxyfumigaclavine C
Stars
DefinitionAn ergot alkaloid that is ergoline substituted by a 2-methylbut-3-en-2-yl group at position 2 and methyl groups at positions 6 and 8 (the 8β stereoisomer). It is isolated from an endophytic fungus, Aspergillus fumigatus, and exhibits potent cytotoxicity against human leukemia cells (K562).
Last Modified27 October 2016
DownloadsMolfile
FormulaC21H28N2
Net Charge0
Average Mass308.469
Monoisotopic Mass308.22525
SMILES[H][C@@]12Cc3c(C(C)(C)C=C)nc4cccc(c34)[C@@]1([H])C[C@@H](C)CN2C
InChIInChI=1S/C21H28N2/c1-6-21(3,4)20-16-11-18-15(10-13(2)12-23(18)5)14-8-7-9-17(22-20)19(14)16/h6-9,13,15,18,22H,1,10-12H2,2-5H3/t13-,15-,18-/m1/s1
InChIKeyGXEMWNLJOIOIIM-DDUZABMNSA-N
Species of MetaboliteComponentSourceComments
Aspergillus fumigatus (ncbitaxon:746128) - PubMed (19256529) An endophytic fungus Strain: CY018
Roles Classification
Biological Roles:
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
9-deacetoxyfumigaclavine C (CHEBI:65724) has functional parent fumigaclavine C (CHEBI:64673)
9-deacetoxyfumigaclavine C (CHEBI:65724) has parent hydride ergoline (CHEBI:38484)
9-deacetoxyfumigaclavine C (CHEBI:65724) has role Aspergillus metabolite (CHEBI:76956)
9-deacetoxyfumigaclavine C (CHEBI:65724) has role antineoplastic agent (CHEBI:35610)
9-deacetoxyfumigaclavine C (CHEBI:65724) is a ergot alkaloid (CHEBI:23943)
IUPAC Name 
(8β)-6,8-dimethyl-2-(2-methylbut-3-en-2-yl)ergoline
Registry NumbersSources
Reaxys:19760285Reaxys
Citations