Cis-(2R*,3S*)-1-(6-Phenylnaphthalene-2-carbonyl)piperazine-2,3-dicarboxylic Acid

ID: ALA1950796

Chembl Id: CHEMBL1950796

PubChem CID: 56945290

Max Phase: Preclinical

Molecular Formula: C23H20N2O5

Molecular Weight: 404.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1NCCN(C(=O)c2ccc3cc(-c4ccccc4)ccc3c2)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C23H20N2O5/c26-21(25-11-10-24-19(22(27)28)20(25)23(29)30)18-9-8-16-12-15(6-7-17(16)13-18)14-4-2-1-3-5-14/h1-9,12-13,19-20,24H,10-11H2,(H,27,28)(H,29,30)/t19-,20+/m0/s1

Standard InChI Key:  WMGWFXOUJQIMSL-VQTJNVASSA-N

Alternative Forms

1. Parent:

   

   ALA1950796

   (2R,3S)-1-(6-phenylnaphthalene-2-carbonyl)piperazine-2,3-dicarboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 404.42

Molecular Weight (Monoisotopic): 404.1372

AlogP: 2.46

#Rotatable Bonds: 4

Polar Surface Area: 106.94

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.58

CX Basic pKa: 7.81

CX LogP: 0.51

CX LogD: -2.86

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -0.31

References

1. Irvine MW, Costa BM, Dlaboga D, Culley GR, Hulse R, Scholefield CL, Atlason P, Fang G, Eaves R, Morley R, Mayo-Martin MB, Amici M, Bortolotto ZA, Donaldson L, Collingridge GL, Molnár E, Monaghan DT, Jane DE..  (2012)  Piperazine-2,3-dicarboxylic acid derivatives as dual antagonists of NMDA and GluK1-containing kainate receptors.,  55  (1): [PMID:22111545] [10.1021/jm201230z]

Source

Source(1):

• Scientific Literature