PL37   Click here for help

GtoPdb Ligand ID: 7896

Synonyms: 19-IIIa [3] | Debio 0827 [1] | Debio-0827
Compound class: Synthetic organic
Comment: PL37 is an investigational, orally available, dual pro-drug inhibitor of neprilysin (a.k.a. neutral endopeptidase or NEP; MME) and aminopeptidase N (APN; ANPEP) [3]. NEP and APN are enkephalin catabolising enzymes (or enkephalinases). Dual ENKephalinase inhibitors such as this one have been ascribed the acronym DENK inhibitor (or DENKi).
PL37 is the non-stereo enantiomer of compound 15 in patent US8247609 [4]. Such dual inhibitors are suggested as a novel mechanism for the control of central and peripheral pain [5], via inhibition of enzymatic degradation of endogenous enkephalins. Such agents could replace the use of opiate analgesics.
2D Structure
Click here for help

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.

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

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.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 20
Topological polar surface area 192.85
Molecular weight 518.16
XLogP 4.08
No. Lipinski's rules broken 1

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
Click here for help

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/)

✖
Canonical SMILES CSCCC(CSSCC(C(=O)NCC(=O)OC(OC(=O)OCC)C)Cc1ccccc1)N
Isomeric SMILES CSCCC(CSSCC(C(=O)NCC(=O)OC(OC(=O)OCC)C)Cc1ccccc1)N
InChI InChI=1S/C22H34N2O6S3/c1-4-28-22(27)30-16(2)29-20(25)13-24-21(26)18(12-17-8-6-5-7-9-17)14-32-33-15-19(23)10-11-31-3/h5-9,16,18-19H,4,10-15,23H2,1-3H3,(H,24,26)
InChI Key BJCNUZJDFWFVBY-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
IUPAC Name Click here for help
1-ethoxycarbonyloxyethyl 2-[[2-[(2-amino-4-methylsulfanylbutyl)disulfanylmethyl]-3-phenylpropanoyl]amino]acetate
Synonyms Click here for help
19-IIIa [3] | Debio 0827 [1] | Debio-0827
Database Links Click here for help
GtoPdb PubChem SID 315661093
PubChem CID 16123252
Search Google for chemical match using the InChIKey BJCNUZJDFWFVBY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BJCNUZJDFWFVBY
UniChem Compound Search for chemical match using the InChIKey BJCNUZJDFWFVBY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BJCNUZJDFWFVBY-UHFFFAOYSA-N