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CHEBI:69407 - pestalamide B

ChEBI IDCHEBI:69407
ChEBI Namepestalamide B
Stars
DefinitionA 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.
Last Modified7 November 2016
DownloadsMolfile
FormulaC18H18N2O5
Net Charge0
Average Mass342.351
Monoisotopic Mass342.12157
SMILESC[C@@H](CC(=O)NC(=O)c1cnc(Cc2ccccc2)cc1=O)C(=O)O
InChIInChI=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
InChIKeyAKUZFSWMFGYDBI-NSHDSACASA-N
Species of MetaboliteComponentSourceComments
Aspergillus basiliensis (ncbitaxon:319629) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 35542
Aspergillus carbonarius (ncbitaxon:40993)
latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 369
latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 346
Aspergillus parasiticus (ncbitaxon:5067) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 465
Aspergillus tubingensis (ncbitaxon:5068) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 4875
Aspergillus ellipticus (ncbitaxon:41066) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 5120
Aspergillus niger (ncbitaxon:5061)
latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 326
latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 1015
Aspergillus japonicus (ncbitaxon:34381) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 2053
Aspergillus ibericus (ncbitaxon:301854) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 35644
Aspergillus aculeatus (ncbitaxon:5053) latex (BTO:0000710) PubMed (21854017) Previous component: resin; Methanolic extract of resin and cell mass Strain: NRRL 5094
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:19412738Reaxys
Citations