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

ID: ALA1950795

Chembl Id: CHEMBL1950795

PubChem CID: 56945289

Max Phase: Preclinical

Molecular Formula: C17H15IN2O5

Molecular Weight: 454.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H15IN2O5/c18-12-4-3-9-7-11(2-1-10(9)8-12)15(21)20-6-5-19-13(16(22)23)14(20)17(24)25/h1-4,7-8,13-14,19H,5-6H2,(H,22,23)(H,24,25)/t13-,14+/m0/s1

Standard InChI Key:  ZTLAEJCVKCGGDN-UONOGXRCSA-N

Alternative Forms

1. Parent:

   

   ALA1950795

   (2R,3S)-1-(6-iodonaphthalene-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: 454.22

Molecular Weight (Monoisotopic): 454.0026

AlogP: 1.40

#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: 2.54

CX Basic pKa: 7.81

CX LogP: -0.25

CX LogD: -3.66

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.59

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