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(RS)-2-Amino-3-(5,6-dichloro-4'-(hydroxymethyl)biphenyl-3-yl)-propanoic Acid

ID: ALA3759809

PubChem CID: 127025768

Max Phase: Preclinical

Molecular Formula: C16H15Cl2NO3

Molecular Weight: 340.21

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  NC(Cc1cc(Cl)c(Cl)c(-c2ccc(CO)cc2)c1)C(=O)O

Standard InChI:  InChI=1S/C16H15Cl2NO3/c17-13-6-10(7-14(19)16(21)22)5-12(15(13)18)11-3-1-9(8-20)2-4-11/h1-6,14,20H,7-8,19H2,(H,21,22)

Standard InChI Key:  MJNYDAQZWNWITE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471    5.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688    5.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -4.9597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    3.1476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  6 12  1  0
 18 19  1  0
 15 18  1  0
 11 20  1  0
 10 21  1  0
  3  8  1  0
  2 22  1  0
M  END

Alternative Forms

  1. Parent:

    ALA3759809

    ---

Associated Targets(non-human)

Grin1 Glutamate NMDA receptor (6467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grik1 Glutamate receptor ionotropic kainate 1 (319 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 340.21Molecular Weight (Monoisotopic): 339.0429AlogP: 3.11#Rotatable Bonds: 5
Polar Surface Area: 83.55Molecular Species: ZWITTERIONHBA: 3HBD: 3
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 1.96CX Basic pKa: 9.42CX LogP: 0.90CX LogD: 0.90
Aromatic Rings: 2Heavy Atoms: 22QED Weighted: 0.78Np Likeness Score: 0.38

References

1. 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]

Source