CHEBI:69407 - pestalamide B

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ChEBI Name pestalamide B
ChEBI ID CHEBI:69407
Definition A member of the class of 4-pyridones that is aspernigrin A (2-benzyl-4-pyridone-5-carboxamide) in which the nitrogen of the carboxamide has been acylated by a (3S)-3-carboxybutanoyl group. It has been isolated from Aspergillus niger and several other Aspergillus species.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H18N2O5
Net Charge 0
Average Mass 342.347
Monoisotopic Mass 342.12157
InChI InChI=1S/C18H18N2O5/c1-11(18(24)25)7-16(22)20-17(23)14-10-19-13(9-15(14)21)8-12-5-3-2-4-6-12/h2-6,9-11H,7-8H2,1H3,(H,19,21)(H,24,25)(H,20,22,23)/t11-/m0/s1
InChIKey AKUZFSWMFGYDBI-NSHDSACASA-N
SMILES C(C1=CC(C(=CN1)C(=O)NC(C[C@@H](C(O)=O)C)=O)=O)C=2C=CC=CC2
Metabolite of Species Details
Aspergillus ibericus (NCBI:txid301854) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 35644 See: PubMed
Aspergillus basiliensis (NCBI:txid319629) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 35542 See: PubMed
Aspergillus japonicus (NCBI:txid34381) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 2053 See: PubMed
Aspergillus carbonarius (NCBI:txid40993) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 346 See: PubMed
Aspergillus carbonarius (NCBI:txid40993) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 369 See: PubMed
Aspergillus ellipticus (NCBI:txid41066) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 5120 See: PubMed
Aspergillus aculeatus (NCBI:txid5053) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 5094 See: PubMed
Aspergillus niger (NCBI:txid5061) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 326 See: PubMed
Aspergillus niger (NCBI:txid5061) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 1015 See: PubMed
Aspergillus parasiticus (NCBI:txid5067) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 465 See: PubMed
Aspergillus tubingensis (NCBI:txid5068) Found in latex (BTO:0000710). Previous component: resin; Methanolic extract of resin and cell mass of strain NRRL 4875 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pestalamide B (CHEBI:69407) has functional parent aspernigrin A (CHEBI:133846)
pestalamide B (CHEBI:69407) has role Aspergillus metabolite (CHEBI:76956)
pestalamide B (CHEBI:69407) is a 4-pyridones (CHEBI:20485)
pestalamide B (CHEBI:69407) is a dicarboximide (CHEBI:35356)
pestalamide B (CHEBI:69407) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(2S)-4-{[(6-benzyl-4-oxo-1,4-dihydropyridin-3-yl)carbonyl]amino}-2-methyl-4-oxobutanoic acid
Registry Number Type Source
19412738 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21854017 PubMed citation Europe PMC
Last Modified
07 November 2016