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dipivefrine   Click here for help

GtoPdb Ligand ID: 7166

Synonyms: Propine®
Approved drug
dipivefrine is an approved drug
Compound class: Synthetic organic
Comment: Dipivefrin is a prodrug of adrenaline/epinephrine.
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 4
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 84.86
Molecular weight 351.2
XLogP 1.72
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 CNCC(c1ccc(c(c1)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)O
Isomeric SMILES CNCC(c1ccc(c(c1)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)O
InChI InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
InChI Key OCUJLLGVOUDECM-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.
Is prodrug? Yes
Active form (±)-adrenaline
IUPAC Name Click here for help
2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
International Nonproprietary Names Click here for help
INN number INN
4429 dipivefrine
Synonyms Click here for help
Propine®
Database Links Click here for help
CAS Registry No. 52365-63-6
ChEMBL Ligand CHEMBL1201262
DrugBank Ligand DB00449
DrugCentral Ligand 922
GtoPdb PubChem SID 178103741
PubChem CID 3105
Search Google for chemical match using the InChIKey OCUJLLGVOUDECM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OCUJLLGVOUDECM
Search PubMed clinical trials dipivefrine
Search PubMed titles dipivefrine
Search PubMed titles/abstracts dipivefrine
UniChem Compound Search for chemical match using the InChIKey OCUJLLGVOUDECM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OCUJLLGVOUDECM-UHFFFAOYSA-N
Wikipedia Dipivefrine