CHEBI:145685 - notoamide C

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ChEBI Name notoamide C
ChEBI ID CHEBI:145685
Definition A notoamide that is 7,7-dimethyl-1,7-dihydropyrano[2,3-g]indol-2(3H)-one which is substituted at position 3 by 3-methylbut-1-en-3-yl and [(3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl]methyl groups (the all-S stereoisomer). Isolated from a mussel-derived Aspergillus species.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
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Formula C26H31N3O4
Net Charge 0
Average Mass 449.551
Monoisotopic Mass 449.23146
InChI InChI=1S/C26H31N3O4/c1-6-24(2,3)26(14-17-22(31)29-13-7-8-18(29)21(30)27-17)16-9-10-19-15(20(16)28-23(26)32)11-12-25(4,5)33-19/h6,9-12,17-18H,1,7-8,13-14H2,2-5H3,(H,27,30)(H,28,32)/t17-,18-,26-/m0/s1
InChIKey KNFZHRYXLWKRSU-XWXLMPLOSA-N
SMILES N12C([C@@H](NC([C@@]1(CCC2)[H])=O)C[C@]3(C(NC4=C3C=CC5=C4C=CC(O5)(C)C)=O)C(C=C)(C)C)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
(via notoamide )
mycotoxin
Poisonous substance produced by fungi.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
(via notoamide )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antifouling biocide
A compound that inhibits the growth of marine organisms.
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ChEBI Ontology
Outgoing notoamide C (CHEBI:145685) has role Aspergillus metabolite (CHEBI:76956)
notoamide C (CHEBI:145685) has role antifouling biocide (CHEBI:51076)
notoamide C (CHEBI:145685) has role mycotoxin (CHEBI:25442)
notoamide C (CHEBI:145685) is a dipeptide (CHEBI:46761)
notoamide C (CHEBI:145685) is a indole alkaloid (CHEBI:38958)
notoamide C (CHEBI:145685) is a notoamide (CHEBI:145690)
notoamide C (CHEBI:145685) is a organic heterotricyclic compound (CHEBI:26979)
notoamide C (CHEBI:145685) is a pyrrolopyrazine (CHEBI:48337)
IUPAC Name
(3S,8aS)-3-{[(3S)-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1,2,3,7-tetrahydropyrano[2,3-g]indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonym Source
notoamide C UniProt
Manual Xrefs Databases
C00039873 KNApSAcK
CPD-17362 MetaCyc
View more database links
Registry Number Type Source
937251-97-3 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
22140279 PubMed citation Europe PMC
22140281 PubMed citation SUBMITTER
22188465 PubMed citation SUBMITTER
23213353 PubMed citation Europe PMC
24532297 PubMed citation Europe PMC
26061478 PubMed citation Europe PMC
26287214 PubMed citation Europe PMC
Last Modified
06 January 2020