CHEBI:16483 - isonocardicin A

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ChEBI Name isonocardicin A
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
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 )
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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)
Synonyms Sources
1-azetidineacetic acid KEGG COMPOUND
isonocardicin A KEGG COMPOUND
Manual Xref Database
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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.