RB101   Click here for help

GtoPdb Ligand ID: 11650

Synonyms: RB 101 | RB-101
Compound class: Synthetic organic
Comment: RB101 is an enkephalinase inhibitor, that is used as a biological tool [2]. It is metabolically cleaved into two active components, each of which inhibits one of the zinc-metallopeptidase enkephalin-degrading enzymes, aminopeptidase N (APN; ANPEP) and neutral endopeptidase (neprilysin; official gene name membrane metalloendopeptidase MME) [1]. Aminopeptidase N/neprilysin inhibition with RB101 induces an elevation in the levels of the two endogenous enkephalins [Met]enkephalin and [Leu]enkephalin. Prodrugs with this mechanism of action are known collectively as Dual Enkephalinase Inhibitors, or DENKIs.
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 5
Hydrogen bond donors 2
Rotatable bonds 19
Topological polar surface area 157.32
Molecular weight 582.2
XLogP 6.54
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 CSCCC(CSSCC(C(=O)N[C@H](C(=O)OCc1ccccc1)Cc1ccccc1)Cc1ccccc1)N
Isomeric SMILES CSCCC(CSSCC(Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1)N
InChI InChI=1S/C31H38N2O3S3/c1-37-18-17-28(32)23-39-38-22-27(19-24-11-5-2-6-12-24)30(34)33-29(20-25-13-7-3-8-14-25)31(35)36-21-26-15-9-4-10-16-26/h2-16,27-29H,17-23,32H2,1H3,(H,33,34)/t27?,28?,29-/m0/s1
InChI Key QXXMSEVVNUSHKJ-PPUMFKDSSA-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
benzyl (2S)-2-[[2-[[(2-amino-4-methylsulfanylbutyl)disulfanyl]methyl]-3-phenylpropanoyl]amino]-3-phenylpropanoate
Synonyms Click here for help
RB 101 | RB-101
Database Links Click here for help
CAS Registry No. 135949-60-9 (source: PubChem)
GtoPdb PubChem SID 442878676
PubChem CID 21119879
Search Google for chemical match using the InChIKey QXXMSEVVNUSHKJ-PPUMFKDSSA-N
Search Google for chemicals with the same backbone QXXMSEVVNUSHKJ
UniChem Compound Search for chemical match using the InChIKey QXXMSEVVNUSHKJ-PPUMFKDSSA-N
UniChem Connectivity Search for chemical match using the InChIKey QXXMSEVVNUSHKJ-PPUMFKDSSA-N