CHEBI:64673 - fumigaclavine C

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ChEBI Name fumigaclavine C
ChEBI ID CHEBI:64673
Definition An ergot alkaloid produced by the fungus Aspergillus fumigatus that is ergoline which is substituted by a 2-methylbut-3-en-2-yl group at position 2, methyl groups at the 6 and 8β positions, and by an acetoxy group at the 9β position.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H30N2O2
Net Charge 0
Average Mass 366.49650
Monoisotopic Mass 366.23073
InChI InChI=1S/C23H30N2O2/c1-7-23(4,5)22-16-11-18-20(15-9-8-10-17(24-22)19(15)16)21(27-14(3)26)13(2)12-25(18)6/h7-10,13,18,20-21,24H,1,11-12H2,2-6H3/t13-,18+,20+,21-/m0/s1
InChIKey OSICWVVWEXKSBD-LFAYTRTRSA-N
SMILES [H][C@@]12Cc3c([nH]c4cccc(c34)[C@@]1([H])[C@@H](OC(C)=O)[C@@H](C)CN2C)C(C)(C)C=C
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing fumigaclavine C (CHEBI:64673) has parent hydride ergoline (CHEBI:38484)
fumigaclavine C (CHEBI:64673) has role metabolite (CHEBI:25212)
fumigaclavine C (CHEBI:64673) is a acetate ester (CHEBI:47622)
fumigaclavine C (CHEBI:64673) is a ergot alkaloid (CHEBI:23943)
fumigaclavine C (CHEBI:64673) is conjugate base of fumigaclavine C(1+) (CHEBI:67147)
Incoming 9-deacetoxyfumigaclavine C (CHEBI:65724) has functional parent fumigaclavine C (CHEBI:64673)
fumigaclavine C(1+) (CHEBI:67147) is conjugate acid of fumigaclavine C (CHEBI:64673)
IUPAC Name
(8β,9β)-6,8-dimethyl-2-(2-methylbut-3-en-2-yl)ergolin-9-yl acetate
Manual Xref Database
CPD-12338 MetaCyc
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Registry Numbers Types Sources
19760287 Reaxys Registry Number Reaxys
62867-47-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15231043 PubMed citation Europe PMC
16023606 PubMed citation Europe PMC
16397874 PubMed citation Europe PMC
16557450 PubMed citation Europe PMC
16902860 PubMed citation Europe PMC
18678866 PubMed citation Europe PMC
19256529 PubMed citation Europe PMC
21762706 PubMed citation Europe PMC
22344643 PubMed citation Europe PMC
350117 PubMed citation Europe PMC
Last Modified
21 December 2012