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methicillin   Click here for help

GtoPdb Ligand ID: 12264

Synonyms: meticillin
Approved drug PDB Ligand
methicillin is an approved drug (FDA (1971))
Compound class: Synthetic organic
Comment: Methicillin/meticillin, is a narrow-spectrum β-lactam antimicrobial compound that was discovered in 1960.
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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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 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 130.47
Molecular weight 380.1
XLogP 1.51
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 COc1cccc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)OC
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)c1c(cccc1OC)OC)C(=O)O)C
InChI InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
InChI Key RJQXTJLFIWVMTO-TYNCELHUSA-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. US FDA (1971)
IUPAC Name Click here for help
(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)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
1103 meticillin
Synonyms Click here for help
meticillin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Methicillin
Other databases
CAS Registry No. 61-32-5 (source: Scifinder)
ChEBI CHEBI:6827
ChEMBL Ligand CHEMBL575
DrugBank Ligand DB01603
DrugCentral Ligand 1744
GtoPdb PubChem SID 473153852
PubChem CID 6087
RCSB PDB Ligand MII
Search Google for chemical match using the InChIKey RJQXTJLFIWVMTO-TYNCELHUSA-N
Search Google for chemicals with the same backbone RJQXTJLFIWVMTO
Search PubMed clinical trials meticillin
Search PubMed titles meticillin
Search PubMed titles/abstracts meticillin
UniChem Compound Search for chemical match using the InChIKey RJQXTJLFIWVMTO-TYNCELHUSA-N
UniChem Connectivity Search for chemical match using the InChIKey RJQXTJLFIWVMTO-TYNCELHUSA-N
Wikipedia Methicillin