(RS)-2-Amino-3-(5,6-dichloro-3'-hydroxybiphenyl-3-yl)-propanoic acid

ID: ALA611036

Chembl Id: CHEMBL611036

PubChem CID: 45101467

Max Phase: Preclinical

Molecular Formula: C15H13Cl2NO3

Molecular Weight: 326.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1cc(Cl)c(Cl)c(-c2cccc(O)c2)c1)C(=O)O

Standard InChI:  InChI=1S/C15H13Cl2NO3/c16-12-5-8(6-13(18)15(20)21)4-11(14(12)17)9-2-1-3-10(19)7-9/h1-5,7,13,19H,6,18H2,(H,20,21)

Standard InChI Key:  ZNFSSBKROKSXNN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA611036

   2-Amino-3-[3,4-dichloro-5-(3-hydroxyphenyl)phenyl]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: 326.18

Molecular Weight (Monoisotopic): 325.0272

AlogP: 3.32

#Rotatable Bonds: 4

Polar Surface Area: 83.55

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.79

CX Basic pKa: 9.26

CX LogP: 1.37

CX LogD: 1.36

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: 0.45

References

1. Szymańska E, Pickering DS, Nielsen B, Johansen TN..  (2009)  3-Substituted phenylalanines as selective AMPA- and kainate receptor ligands.,  17  (17): [PMID:19656686] [10.1016/j.bmc.2009.07.021]

2. Szymanska E, Frydenvang K, Pickering DS, Krintel C, Nielsen B, Kooshki A, Zachariassen LG, Olsen L, Kastrup JS, Johansen TN..  (2016)  Studies on Aryl-Substituted Phenylalanines: Synthesis, Activity, and Different Binding Modes at AMPA Receptors.,  59  (1): [PMID:26653877] [10.1021/acs.jmedchem.5b01666]

3. Szymańska E, Nielsen B, Johansen TN, Cuñado Moral AM, Pickering DS, Szczepańska K, Mickowska A, Kieć-Kononowicz K..  (2017)  Pharmacological characterization and binding modes of novel racemic and optically active phenylalanine-based antagonists of AMPA receptors.,  138  [PMID:28738307] [10.1016/j.ejmech.2017.07.007]

Source

Source(1):

• Scientific Literature