(2R,3S)-1-(7-Bromo-9,10-dihydro-phenanthrene-2-carbonyl)-piperazine-2,3-dicarboxylic acid

ID: ALA192728

Chembl Id: CHEMBL192728

PubChem CID: 11351608

Max Phase: Preclinical

Molecular Formula: C21H19BrN2O5

Molecular Weight: 459.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1NCCN(C(=O)c2ccc3c(c2)CCc2cc(Br)ccc2-3)[C@H]1C(=O)O

Standard InChI:  InChI=1S/C21H19BrN2O5/c22-14-4-6-16-12(10-14)2-1-11-9-13(3-5-15(11)16)19(25)24-8-7-23-17(20(26)27)18(24)21(28)29/h3-6,9-10,17-18,23H,1-2,7-8H2,(H,26,27)(H,28,29)/t17-,18+/m0/s1

Standard InChI Key:  HRIUAKLNJFGFHN-ZWKOTPCHSA-N

Alternative Forms

1. Parent:

   

   ALA192728

   (2R,3S)-1-(7-Bromo-9,10-dihydro-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: 459.30

Molecular Weight (Monoisotopic): 458.0477

AlogP: 2.17

#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: 2.62

CX Basic pKa: 7.81

CX LogP: 0.85

CX LogD: -2.53

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.27

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