Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-15 02:26:58 UTC
Update Date2025-10-07 16:05:42 UTC
Metabolite IDMMDBc0010190
Metabolite Identification
Common NamePenidiamide
DescriptionPenidiamide is a metabolite belonging to the class of tripetides. It consists of dehydrotryptamine, glycine, and anthranilic acid linked by two amide bonds, along with an oxindole moiety. This compound was isolated from submerged cultures of Penicillium sp. using preparative chromatography (PMID:38814060 ). The structure of penidiamide was elucidated through spectroscopic methods, confirming its unique composition (PMID:9528122 ). In terms of biological activity, penidiamide exhibits preferential inhibition of human synovial phospholipase A2, with an IC50 value of 30 microM, while oxindole shows a significantly higher IC50 of 380 microM (PMID:9528122 ). Although penidiamide demonstrates weak antibacterial activity, no antimicrobial activity was detected for oxindole (PMID:9528122 ). This highlights penidiamide's potential relevance in biochemical pathways, particularly concerning phospholipase inhibition, while also indicating limited antibacterial properties.
Structure
SynonymsNot Available
Molecular FormulaC19H18N4O2
Average Mass334.379
Monoisotopic Mass334.142975836
IUPAC Name2-{[(2-aminophenyl)(hydroxy)methylidene]amino}-N-[(E)-2-(1H-indol-3-yl)ethenyl]ethanimidic acid
Traditional Name2-{[(2-aminophenyl)(hydroxy)methylidene]amino}-N-[(E)-2-(1H-indol-3-yl)ethenyl]ethanimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(N=C(O)CN=C(O)C1=CC=CC=C1N)=C(\[H])C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C19H18N4O2/c20-16-7-3-1-6-15(16)19(25)23-12-18(24)21-10-9-13-11-22-17-8-4-2-5-14(13)17/h1-11,22H,12,20H2,(H,21,24)(H,23,25)/b10-9+
InChI KeyDCQDGRBMXXRGIN-MDZDMXLPSA-N