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 antibacterial.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)[C@@H](C3=CC=C(C=C3)O)N
Isomeric SMILES O=C([C@@H](C1=CC=C(C=C1)O)N)N[C@@H]2C(=O)N3[C@@H]2SC([C@@H]3C(=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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1974))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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
Specialist databases
Antibiotic DB Antibiotic DB Database logo Amoxicillin
Other databases
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
Search Google for chemical match using the InChIKey LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Search Google for chemicals with the same backbone LSQZJLSUYDQPKJ
Search PubMed clinical trials amoxicillin
Search PubMed titles amoxicillin
Search PubMed titles/abstracts amoxicillin
UniChem Compound Search for chemical match using the InChIKey LSQZJLSUYDQPKJ-NJBDSQKTSA-N
UniChem Connectivity Search for chemical match using the InChIKey LSQZJLSUYDQPKJ-NJBDSQKTSA-N