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

ID: ALA425185

Chembl Id: CHEMBL425185

Cas Number: 850080-36-3

PubChem CID: 11199785

Max Phase: Preclinical

Molecular Formula: C21H18N2O5

Molecular Weight: 378.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1NCCN(C(=O)c2ccc3c(ccc4ccccc43)c2)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C21H18N2O5/c24-19(23-10-9-22-17(20(25)26)18(23)21(27)28)14-7-8-16-13(11-14)6-5-12-3-1-2-4-15(12)16/h1-8,11,17-18,22H,9-10H2,(H,25,26)(H,27,28)/t17-,18-/m1/s1

Standard InChI Key:  IWWXIZOMXGOTPP-QZTJIDSGSA-N

Alternative Forms

1. Parent:

   

   ALA425185

   (2R,3R)-1-(Phenanthrene-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: 378.38

Molecular Weight (Monoisotopic): 378.1216

AlogP: 1.94

#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: 2.69

CX Basic pKa: 7.81

CX LogP: -0.10

CX LogD: -3.43

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -0.26

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