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CHEBI:9391 - talampicillin

ChEBI IDCHEBI:9391
ChEBI Nametalampicillin
Stars
DefinitionA penicillanic acid ester that is the 1-phthalidyl ester of ampicillin. It is a prodrug of ampicillin.
Last Modified14 March 2018
DownloadsMolfile
FormulaC24H23N3O6S
Net Charge0
Average Mass481.530
Monoisotopic Mass481.13076
SMILES[H][C@]12SC(C)(C)[C@H](C(=O)OC3OC(=O)c4ccccc43)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
InChIInChI=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
InChIKeySOROUYSPFADXSN-SUWVAFIASA-N
Roles Classification
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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
TalampicillinKEGG COMPOUND
Manual XrefsDatabases
2554DrugCentral
C11751KEGG COMPOUND
C13978KEGG COMPOUND
D02201KEGG DRUG
D08557KEGG DRUG
DE228012Patent
LSM-1304LINCS
US3860579Patent
US3951954Patent
Registry NumbersSources
CAS:47747-56-8KEGG COMPOUND
Citations