CHEBI:72763 - fumitremorgin C

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ChEBI Name fumitremorgin C
ChEBI ID CHEBI:72763
Definition An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KAX
Supplier Information
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Formula C22H25N3O3
Net Charge 0
Average Mass 379.45220
Monoisotopic Mass 379.18959
InChI InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
InChIKey DBEYVIGIPJSTOR-FHWLQOOXSA-N
SMILES [H][C@@]12CCCN1C(=O)[C@]1([H])Cc3c([nH]c4cc(OC)ccc34)[C@H](C=C(C)C)N1C2=O
Roles Classification
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
breast cancer resistance protein inhibitor
Any inhibitor of breast cancer resistance protein (ABCG2).
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 fumitremorgin C (CHEBI:72763) has role breast cancer resistance protein inhibitor (CHEBI:72771)
fumitremorgin C (CHEBI:72763) has role mycotoxin (CHEBI:25442)
fumitremorgin C (CHEBI:72763) is a aromatic ether (CHEBI:35618)
fumitremorgin C (CHEBI:72763) is a indole alkaloid (CHEBI:38958)
fumitremorgin C (CHEBI:72763) is a organic heteropentacyclic compound (CHEBI:38164)
Incoming 12,13-dihydroxyfumitremorgin C (CHEBI:72764) has functional parent fumitremorgin C (CHEBI:72763)
IUPAC Name
(5aS,12S,14aS)-9-methoxy-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
Synonyms Sources
fumitremorgin C UniProt
tryptoquivaline ChEBI
Manual Xrefs Databases
HMDB0038642 HMDB
WO2007059330 Patent
View more database links
Registry Numbers Types Sources
118974-02-0 CAS Registry Number HMDB
4586854 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19226505 PubMed citation SUBMITTER
19763315 PubMed citation SUBMITTER
20655304 PubMed citation Europe PMC
22344914 PubMed citation Europe PMC
Last Modified
14 March 2013