CHEBI:52060 - metampicillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name metampicillin
ChEBI ID CHEBI:52060
Definition A penicillin compound having a 6β-(2R)-2-(methylideneamino)-2-phenylacetamido side-group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C17H19N3O4S
Net Charge 0
Average Mass 361.41500
Monoisotopic Mass 361.110
InChI InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1
InChIKey FZECHKJQHUVANE-MCYUEQNJSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=C)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): 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 metampicillin (CHEBI:52060) is a penicillin (CHEBI:17334)
metampicillin (CHEBI:52060) is conjugate acid of metampicillin(1−) (CHEBI:52062)
Incoming metampicillin(1−) (CHEBI:52062) is conjugate base of metampicillin (CHEBI:52060)
IUPAC Name
6β-[(2R)-2-(methylideneamino)-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylic acid
INN Source
metampicillin KEGG DRUG
Synonyms Sources
(2S,5R,6R)-3,3-dimethyl-6-{[(2R)-2-(methylideneamino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6β-[(2R)-2-(methylideneamino)-2-phenylacetamido]penicillanic acid ChEBI
Database Links Databases
1718 DrugCentral
BE661232 Patent
D07234 KEGG DRUG
GB1081093 Patent
LSM-15186 LINCS
Metampicillin Wikipedia
View more database links
Registry Number Type Source
6489-97-0 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
349485 PubMed citation Europe PMC
4556172 PubMed citation Europe PMC
4574199 PubMed citation Europe PMC
4775221 PubMed citation Europe PMC
5439760 PubMed citation Europe PMC
5564953 PubMed citation Europe PMC
Last Modified
22 February 2017