(RS)-3'-(2-Amino-2-carboxyethyl)biphenyl-3-carboxylic acid

ID: ALA609876

PubChem CID: 45101472

Max Phase: Preclinical

Molecular Formula: C16H15NO4

Molecular Weight: 285.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1cccc(-c2cccc(C(=O)O)c2)c1)C(=O)O

Standard InChI:  InChI=1S/C16H15NO4/c17-14(16(20)21)8-10-3-1-4-11(7-10)12-5-2-6-13(9-12)15(18)19/h1-7,9,14H,8,17H2,(H,18,19)(H,20,21)

Standard InChI Key:  MWBSOXIHLRVCIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    2.7652   -7.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641   -8.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789   -8.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1953   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -7.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4771   -6.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069   -8.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069   -9.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6211   -9.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3359   -9.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3320   -8.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -8.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4746   -6.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7589   -5.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565   -4.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0457   -6.1206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -4.4664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -4.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0443   -8.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7609   -8.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0401   -7.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  2  0
 11 12  2  0
 12  7  1  0
  4  7  1  0
  6  1  1  0
  6 13  1  0
  1  2  2  0
 13 14  1  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 14 16  1  0
 15 17  1  0
  8  9  1  0
 15 18  2  0
  4  5  1  0
 11 19  1  0
  9 10  2  0
 19 20  1  0
  2  3  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609876

   3-[3-(2-Amino-2-carboxyethyl)phenyl]benzoic 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: 285.30

Molecular Weight (Monoisotopic): 285.1001

AlogP: 2.01

#Rotatable Bonds: 5

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.18

CX Basic pKa: 9.44

CX LogP: 0.05

CX LogD: -2.88

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.78

Np Likeness Score: 0.19

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. Szymańska E, Chałupnik P, Szczepańska K, Cuñado Moral AM, Pickering DS, Nielsen B, Johansen TN, Kieć-Kononowicz K..  (2016)  Design, synthesis and structure-activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands.,  26  (22): [PMID:27765511] [10.1016/j.bmcl.2016.09.075]

Source

Source(1):

• Scientific Literature