(2R,3S)-1-Phenanthren-2-ylmethyl-piperazine-2,3-dicarboxylic acid

ID: ALA192957

Chembl Id: CHEMBL192957

PubChem CID: 11210724

Max Phase: Preclinical

Molecular Formula: C21H20N2O4

Molecular Weight: 364.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1NCCN(Cc2ccc3c(ccc4ccccc43)c2)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C21H20N2O4/c24-20(25)18-19(21(26)27)23(10-9-22-18)12-13-5-8-17-15(11-13)7-6-14-3-1-2-4-16(14)17/h1-8,11,18-19,22H,9-10,12H2,(H,24,25)(H,26,27)/t18-,19+/m0/s1

Standard InChI Key:  HMWHYVPVLJQNRD-RBUKOAKNSA-N

Alternative Forms

1. Parent:

   

   ALA192957

   (2R,3S)-1-Phenanthren-2-ylmethyl-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: 364.40

Molecular Weight (Monoisotopic): 364.1423

AlogP: 2.30

#Rotatable Bonds: 4

Polar Surface Area: 89.87

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.51

CX Basic pKa: 9.22

CX LogP: 0.18

CX LogD: -2.06

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.17

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