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PL265   Click here for help

GtoPdb Ligand ID: 9090

Synonyms: compound 2a [PMID: 25692029]
Compound class: Synthetic organic
Comment: PL265 is a preclinical, long-acting dual ENKephalinase inhibitor (DENKi), with analgesic potential [1]. See also PL37. PL265 has been developed as a novel therapeutic for control of intractable cancer pain. It is 'Example 4' claimed in patent US2014161839 [2].
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 11
Hydrogen bond donors 4
Rotatable bonds 17
Topological polar surface area 178.14
Molecular weight 562.21
XLogP 3.02
No. Lipinski's rules broken 2

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 O=C(NC(P(=O)(CC(C(=O)NC(C(=O)O)C)Cc1ccc(cc1)c1ccccc1)O)C)OCOC(=O)C(C)C
Isomeric SMILES O=C(N[C@H](P(=O)(C[C@H](C(=O)N[C@H](C(=O)O)C)Cc1ccc(cc1)c1ccccc1)O)C)OCOC(=O)C(C)C
InChI InChI=1S/C27H35N2O9P/c1-17(2)26(33)37-16-38-27(34)29-19(4)39(35,36)15-23(24(30)28-18(3)25(31)32)14-20-10-12-22(13-11-20)21-8-6-5-7-9-21/h5-13,17-19,23H,14-16H2,1-4H3,(H,28,30)(H,29,34)(H,31,32)(H,35,36)/t18-,19+,23+/m0/s1
InChI Key HLACXNCYLIKGES-YCRNBWNJSA-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
Is prodrug? Yes
Active form compound 1a [PMID: 25692029]
IUPAC Name Click here for help
(2S)-2-[[(2S)-2-[[hydroxy-[(1R)-1-(2-methylpropanoyloxymethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-(4-phenylphenyl)propanoyl]amino]propanoic acid
Synonyms Click here for help
compound 2a [PMID: 25692029]
Database Links Click here for help
GtoPdb PubChem SID 315661175
PubChem CID 58277249
Search Google for chemical match using the InChIKey HLACXNCYLIKGES-YCRNBWNJSA-N
Search Google for chemicals with the same backbone HLACXNCYLIKGES
UniChem Compound Search for chemical match using the InChIKey HLACXNCYLIKGES-YCRNBWNJSA-N
UniChem Connectivity Search for chemical match using the InChIKey HLACXNCYLIKGES-YCRNBWNJSA-N