metampicillin   Click here for help

GtoPdb Ligand ID: 12274

Synonyms: methampicillin | methylenampicillin | Micinovo® | Viderpen®
Compound class: Synthetic organic
Comment: Metampicillin is a penicillin belonging to the β-lactam class of antibacterial compounds. It is hydrolysed to ampicillin in the acidic conditions within the stomach [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 124.37
Molecular weight 361.11
XLogP 1.4
No. Lipinski's rules broken 0
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Canonical SMILES C=N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)N=C)C(=O)O)C
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
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form ampicillin
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
2570 metampicillin
Synonyms Click here for help
methampicillin | methylenampicillin | Micinovo® | Viderpen®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Metampicillin, methylenampicillin
Other databases
CAS Registry No. 6489-97-0 (source: Scifinder)
ChEMBL Ligand CHEMBL1908324
DrugBank Ligand DB13836
DrugCentral Ligand 1718
GtoPdb PubChem SID 473153862
PubChem CID 6713928
Search Google for chemical match using the InChIKey FZECHKJQHUVANE-MCYUEQNJSA-N
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UniChem Compound Search for chemical match using the InChIKey FZECHKJQHUVANE-MCYUEQNJSA-N
UniChem Connectivity Search for chemical match using the InChIKey FZECHKJQHUVANE-MCYUEQNJSA-N