amoxicillin   

GtoPdb Ligand ID: 10895

Synonyms: Amoxil® | BRL-2333 | co-amoxiclav (amoxicillin + clavulanic acid) | Moxatag® | NSC-277174 | Trimox®
amoxicillin is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Amoxicillin is a widely used penicillin class antibiotic.
2D Structure
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Physico-chemical Properties
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
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
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
(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
INN number INN
3230 amoxicillin
Synonyms
Amoxil® | BRL-2333 | co-amoxiclav (amoxicillin + clavulanic acid) | Moxatag® | NSC-277174 | Trimox®
Database Links
BindingDB Ligand 50350464
CAS Registry No. 26787-78-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL1082
DrugBank Ligand DB01060
GtoPdb PubChem SID 405560336
PubChem CID 33613
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