CHEBI:16483 - isonocardicin A

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ChEBI Name isonocardicin A
ChEBI ID CHEBI:16483
Definition A nocardicin in which the β-lactam moiety is substituted at position 1 by a carboxy(4-hydroxyphenyl)methyl group and at position 3 by a [(2Z)-2-(hydroxyimino)-2-(4-hydroxyphenyl)acetyl]nitrilo group in which the phenolic hydroxy group is substituted by a (3S)-3-amino-3-carboxypropyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:24904, CHEBI:6033, CHEBI:14470
Supplier Information
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Formula C23H24N4O9
Net Charge 0
Average Mass 500.459
Monoisotopic Mass 500.15433
InChI InChI=1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18-/t16-,17-,19+/m0/s1
InChIKey CTNZOGJNVIFEBA-MOKAZRKYSA-N
SMILES N1(C([C@H](C1)NC(/C(/C=2C=CC(OCC[C@@H](C(=O)O)N)=CC2)=N\O)=O)=O)[C@@H](C(O)=O)C3=CC=C(C=C3)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 )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing isonocardicin A (CHEBI:16483) has functional parent D-4-hydroxyphenylglycine (CHEBI:15695)
isonocardicin A (CHEBI:16483) has functional parent L-homoserine (CHEBI:15699)
isonocardicin A (CHEBI:16483) is a aromatic ether (CHEBI:35618)
isonocardicin A (CHEBI:16483) is a dicarboxylic acid (CHEBI:35692)
isonocardicin A (CHEBI:16483) is a nocardicin (CHEBI:25572)
isonocardicin A (CHEBI:16483) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
isonocardicin A (CHEBI:16483) is a phenols (CHEBI:33853)
isonocardicin A (CHEBI:16483) is tautomer of isonocardicin A zwitterion (CHEBI:142510)
Incoming isonocardicin A zwitterion (CHEBI:142510) is tautomer of isonocardicin A (CHEBI:16483)
IUPAC Name
O-{4-[(1Z)-2-({(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}amino)-N-hydroxy-2-oxoethanimidoyl]phenyl}-L-homoserine
Synonyms Sources
1-azetidineacetic acid KEGG COMPOUND
isonocardicin A KEGG COMPOUND
Manual Xref Database
C00927 KEGG COMPOUND
View more database links
Registry Number Type Source
5324091 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15252031 PubMed citation Europe PMC
Last Modified
07 November 2018
General Comment
2018-11-07 Relevant articles: Isenring, H.P. and Hofheinz, W. (1983) A total synthesis of nocardicins. Tetrahedron, 39(15), 2591-2597.