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Substrate Report for: Ampicillin

Ampicillin is a broad-spectrum, beta-lactam penicillin antibiotic. Ampicillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. This interrupts bacterial cell wall synthesis.


General
Type Antibiotic
Chemical_Nomenclature (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
Canonical SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
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
Other name(s) Aminobenzylpenicillin ; Ampicillin acid ; Amcill ; Ampicilline ; Polycillin
________________________________________________________________________________________________
MW|349.40
Formula|C16H19N3O4S
CAS_number|
PubChem|6249
UniChem|AVKUERGKIZMTKX-NJBDSQKTSA-N
IUPHAR|
Wikipedia|Ampicillin

Target
Families | Ampicillin ligand of proteins in family: Cocaine_esterase, Peptidase_S15
Stucture | 1 structure: 1NX9: Acetobacter turbidans alpha-amino acid ester hydrolase S205A mutant complexed with ampicillin
Protein | xanax-GAA, acepa-AEHA

References:
Search PubMed for references concerning: Ampicillin
    Title: Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin
    Blum JK, Bommarius AS
    Ref: J Mol Catal B Enzym, 67:21, 2010 : PubMed

            

    Title: Acetobacter turbidans alpha-amino acid ester hydrolase: how a single mutation improves an antibiotic-producing enzyme
    Barends TR, Polderman-Tijmes JJ, Jekel PA, Williams C, Wybenga G, Janssen DB, Dijkstra BW
    Ref: Journal of Biological Chemistry, 281:5804, 2006 : PubMed