GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

phenylalanine arginine beta-naphthylamide   Click here for help

GtoPdb Ligand ID: 14476

Synonyms: MC-207,110 | PAβN | phenylalanyl arginyl β-naphthylamide
PDB Ligand
Compound class: Synthetic organic
Comment: Phenylalanine arginine beta-naphthylamide (PAβN) is a peptidomimetic that acts as a bacterial efflux pump inhibitor (EPI). It demonstrates potent activity against the resistance-nodulation-division (RND) family of efflux pumps of Gram-negative bacteria [1-2].
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 5
Rotatable bonds 12
Topological polar surface area 148.62
Molecular weight 446.55
XLogP 1.36
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
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 C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)NC2=CC3=C(C=CC=C3)C=C2)N
Isomeric SMILES C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)NC2=CC3=CC=CC=C3C=C2)N
InChI InChI=1S/C25H30N6O2/c26-21(15-17-7-2-1-3-8-17)23(32)31-22(11-6-14-29-25(27)28)24(33)30-20-13-12-18-9-4-5-10-19(18)16-20/h1-5,7-10,12-13,16,21-22H,6,11,14-15,26H2,(H,30,33)(H,31,32)(H4,27,28,29)/t21-,22-/m0/s1
InChI Key ZNHUFUZDUQRKBB-VXKWHMMOSA-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
(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)-N-naphthalen-2-ylpentanamide
Synonyms Click here for help
MC-207,110 | PAβN | phenylalanyl arginyl β-naphthylamide
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo MC-207,110
Other databases
CAS Registry No. 115871-02-8 (source: Scifinder)
ChEBI CHEBI:6611
ChEMBL Ligand CHEMBL56252
PubChem CID 443301
RCSB PDB Ligand MC2
Search Google for chemical match using the InChIKey ZNHUFUZDUQRKBB-VXKWHMMOSA-N
Search Google for chemicals with the same backbone ZNHUFUZDUQRKBB
UniChem Compound Search for chemical match using the InChIKey ZNHUFUZDUQRKBB-VXKWHMMOSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZNHUFUZDUQRKBB-VXKWHMMOSA-N