CHEBI:9391 - talampicillin

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ChEBI Name talampicillin
ChEBI ID CHEBI:9391
Definition A penicillanic acid ester that is the 1-phthalidyl ester of ampicillin. It is a prodrug of ampicillin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H23N3O6S
Net Charge 0
Average Mass 481.52100
Monoisotopic Mass 481.131
InChI InChI=1S/C24H23N3O6S/c1-24(2)17(22(31)33-23-14-11-7-6-10-13(14)21(30)32-23)27-19(29)16(20(27)34-24)26-18(28)15(25)12-8-4-3-5-9-12/h3-11,15-17,20,23H,25H2,1-2H3,(H,26,28)/t15-,16-,17+,20-,23?/m1/s1
InChIKey SOROUYSPFADXSN-SUWVAFIASA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(=O)OC1OC(=O)c2ccccc12
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing talampicillin (CHEBI:9391) has functional parent o-phthalaldehydic acid (CHEBI:495639)
talampicillin (CHEBI:9391) has functional parent ampicillin (CHEBI:28971)
talampicillin (CHEBI:9391) has role prodrug (CHEBI:50266)
talampicillin (CHEBI:9391) is a penicillanic acid ester (CHEBI:51212)
Incoming talampicillin hydrochloride (CHEBI:34993) has functional parent talampicillin (CHEBI:9391)
IUPAC Name
3-oxo-1,3-dihydro-2-benzofuran-1-yl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Synonym Source
Talampicillin KEGG COMPOUND
Database Links Databases
2554 DrugCentral
C11751 KEGG COMPOUND
C13978 KEGG COMPOUND
D02201 KEGG DRUG
D08557 KEGG DRUG
DE228012 Patent
LSM-1304 LINCS
US3860579 Patent
US3951954 Patent
View more database links
Registry Number Type Source
47747-56-8 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
12026108 PubMed citation Europe PMC
1253699 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
328109 PubMed citation Europe PMC
776328 PubMed citation Europe PMC
974505 PubMed citation Europe PMC
Last Modified
14 March 2018