CHEBI:28971 - ampicillin

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ChEBI Name ampicillin
ChEBI ID CHEBI:28971
Definition A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40648, CHEBI:45042, CHEBI:2683, CHEBI:22536
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Formula C16H19N3O4S
Net Charge 0
Average Mass 349.40500
Monoisotopic Mass 349.110
InChI InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChIKey AVKUERGKIZMTKX-NJBDSQKTSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ampicillin (CHEBI:28971) has role antibacterial drug (CHEBI:36047)
ampicillin (CHEBI:28971) is a β-lactam antibiotic (CHEBI:27933)
ampicillin (CHEBI:28971) is a penicillin (CHEBI:17334)
ampicillin (CHEBI:28971) is conjugate acid of ampicillin(1−) (CHEBI:50658)
Incoming ampicilloyl-butylamine (CHEBI:55473) has functional parent ampicillin (CHEBI:28971)
bacampicillin (CHEBI:2968) has functional parent ampicillin (CHEBI:28971)
epicillin (CHEBI:58974) has functional parent ampicillin (CHEBI:28971)
lenampicillin (CHEBI:135748) has functional parent ampicillin (CHEBI:28971)
pivampicillin (CHEBI:8255) has functional parent ampicillin (CHEBI:28971)
sultamicillin (CHEBI:51770) has functional parent ampicillin (CHEBI:28971)
talampicillin (CHEBI:9391) has functional parent ampicillin (CHEBI:28971)
ampicillin trihydrate (CHEBI:31209) has part ampicillin (CHEBI:28971)
ampicillin(1−) (CHEBI:50658) is conjugate base of ampicillin (CHEBI:28971)
ampicilloyl group (CHEBI:53704) is substituent group from ampicillin (CHEBI:28971)
IUPAC Name
6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylic acid
INNs Sources
ampicilina ChemIDplus
ampicillin ChemIDplus
ampicilline ChemIDplus
ampicillinum ChemIDplus
Synonyms Sources
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID PDBeChem
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid PDBeChem
6-(D-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ChemIDplus
ABPC ChEBI
aminobenzylpenicillin DrugBank
AMP ChEBI
Ampicillin KEGG COMPOUND
ampicillin acid DrugBank
ampicillin anhydrous DrugBank
Anhydrous ampicillin KEGG COMPOUND
AP ChEBI
D-(−)-6-(α-aminophenylacetamido)penicillanic acid ChemIDplus
D-(−)-ampicillin ChemIDplus
Manual Xrefs Databases
1849 VSDB
198 DrugCentral
1H8S PDB
AIC PDBeChem
Ampicillin Wikipedia
C06574 KEGG COMPOUND
D00204 KEGG DRUG
DB00415 DrugBank
GB902703 Patent
HMDB0014559 HMDB
LSM-5761 LINCS
PN1 PDBeChem
US2985648 Patent
US3157640 Patent
View more database links
Registry Numbers Types Sources
4300240 Reaxys Registry Number Reaxys
4300240 Beilstein Registry Number Beilstein
69-53-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
15 March 2018