(RS)-2-Amino-3-(2-(2-carboxyethyl)-5-chloro-4-nitrophenyl)propionic Acid

ID: ALA1835336

Chembl Id: CHEMBL1835336

PubChem CID: 56593692

Max Phase: Preclinical

Molecular Formula: C12H13ClN2O6

Molecular Weight: 316.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1cc(Cl)c([N+](=O)[O-])cc1CCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C12H13ClN2O6/c13-8-3-7(4-9(14)12(18)19)6(1-2-11(16)17)5-10(8)15(20)21/h3,5,9H,1-2,4,14H2,(H,16,17)(H,18,19)

Standard InChI Key:  DRCLPFURMHGQPC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1835336

   2-Amino-3-[2-(2-carboxyethyl)-5-chloro-4-nitrophenyl]propanoic 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: 316.70

Molecular Weight (Monoisotopic): 316.0462

AlogP: 1.22

#Rotatable Bonds: 7

Polar Surface Area: 143.76

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.28

CX Basic pKa: 9.34

CX LogP: -0.63

CX LogD: -3.91

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: -0.06

References

1. Szymańska E, Frydenvang K, Contreras-Sanz A, Pickering DS, Frola E, Serafimoska Z, Nielsen B, Kastrup JS, Johansen TN..  (2011)  A new phenylalanine derivative acts as an antagonist at the AMPA receptor GluA2 and introduces partial domain closure: synthesis, resolution, pharmacology, and crystal structure.,  54  (20): [PMID:21923187] [10.1021/jm200862h]

2. Sköld N, Nielsen B, Olsen J, Han L, Olsen L, Madsen U, Kristensen JL, Pickering DS, Johansen TN..  (2014)  Design, synthesis and in vitro pharmacology of GluK1 and GluK3 antagonists. Studies towards the design of subtype-selective antagonists through 2-carboxyethyl-phenylalanines with substituents interacting with non-conserved residues in the GluK binding sites.,  22  (19): [PMID:25172149] [10.1016/j.bmc.2014.07.045]

Source

Source(1):

• Scientific Literature