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

ID: ALA190724

Chembl Id: CHEMBL190724

PubChem CID: 11163920

Max Phase: Preclinical

Molecular Formula: C17H16N2O5

Molecular Weight: 328.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1NCCN(C(=O)c2ccc3ccccc3c2)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C17H16N2O5/c20-15(12-6-5-10-3-1-2-4-11(10)9-12)19-8-7-18-13(16(21)22)14(19)17(23)24/h1-6,9,13-14,18H,7-8H2,(H,21,22)(H,23,24)/t13-,14+/m0/s1

Standard InChI Key:  GOTATFFBYNVNIS-UONOGXRCSA-N

Alternative Forms

1. Parent:

   

   ALA190724

   (2R,3S)-1-(Naphthalene-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: 328.32

Molecular Weight (Monoisotopic): 328.1059

AlogP: 0.79

#Rotatable Bonds: 3

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: 2.61

CX Basic pKa: 7.81

CX LogP: -1.14

CX LogD: -4.52

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: -0.34

References

1. Morley RM, Tse HW, Feng B, Miller JC, Monaghan DT, Jane DE..  (2005)  Synthesis and pharmacology of N1-substituted piperazine-2,3-dicarboxylic acid derivatives acting as NMDA receptor antagonists.,  48  (7): [PMID:15801853] [10.1021/jm0492498]

2. 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