procaine   Click here for help

GtoPdb Ligand ID: 4291

Synonyms: Novocain®
Approved drug
procaine is an approved drug (FDA (1972))
Compound class: Synthetic organic
Comment: Procaine was approved by the FDA in combination with penicillin in 1948.
Marketed formulations may contain procaine hydrochloride (PubChem CID 5795). In the WHO Essential Medicines list as procaine benzylpenicillin.
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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 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 55.56
Molecular weight 236.15
XLogP 1.84
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 CCN(CCOC(=O)c1ccc(cc1)N)CC
Isomeric SMILES CCN(CCOC(=O)c1ccc(cc1)N)CC
InChI InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3
InChI Key MFDFERRIHVXMIY-UHFFFAOYSA-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 (1972)
IUPAC Name Click here for help
2-(diethylamino)ethyl 4-aminobenzoate
International Nonproprietary Names Click here for help
INN number INN
975 procaine
Synonyms Click here for help
Novocain®
Database Links Click here for help
CAS Registry No. 59-46-1 (source: Scifinder)
ChEMBL Ligand CHEMBL569
DrugBank Ligand DB00721
DrugCentral Ligand 2271
GtoPdb PubChem SID 178101108
PubChem CID 4914
Search Google for chemical match using the InChIKey MFDFERRIHVXMIY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MFDFERRIHVXMIY
Search PubMed clinical trials procaine
Search PubMed titles procaine
Search PubMed titles/abstracts procaine
UniChem Compound Search for chemical match using the InChIKey MFDFERRIHVXMIY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MFDFERRIHVXMIY-UHFFFAOYSA-N
Wikipedia Procaine

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MedChemExpress
Procaine (links to external site)
Cat. No. HY-B0546