amoxicillin   Click here for help

GtoPdb Ligand ID: 10895

Synonyms: Amoxil® | BRL-2333 | co-amoxiclav (amoxicillin + clavulanic acid) | Moxatag® | NSC-277174 | Trimox®
Approved drug
amoxicillin is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Amoxicillin is a widely used penicillin class antibiotic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 158.26
Molecular weight 365.1
XLogP -2.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
InChI Key LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1974))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3230 amoxicillin
Synonyms Click here for help
Amoxil® | BRL-2333 | co-amoxiclav (amoxicillin + clavulanic acid) | Moxatag® | NSC-277174 | Trimox®
Database Links Click here for help
BindingDB Ligand 50350464
CAS Registry No. 26787-78-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL1082
DrugBank Ligand DB01060
DrugCentral Ligand 192
GtoPdb PubChem SID 405560336
PubChem CID 33613
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