(RS)-4-(3-(2-Amino-2-carboxyethyl)benzyl)benzoic acid

ID: ALA608107

PubChem CID: 46227023

Max Phase: Preclinical

Molecular Formula: C17H17NO4

Molecular Weight: 299.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1cccc(Cc2ccc(C(=O)O)cc2)c1)C(=O)O

Standard InChI:  InChI=1S/C17H17NO4/c18-15(17(21)22)10-13-3-1-2-12(9-13)8-11-4-6-14(7-5-11)16(19)20/h1-7,9,15H,8,10,18H2,(H,19,20)(H,21,22)

Standard InChI Key:  FMEJMLGDYSKABO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -4.0001   -6.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -7.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2811   -7.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -7.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732   -6.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -6.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2953   -5.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -5.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -4.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7301   -3.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8506   -7.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1391   -7.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4245   -7.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2866   -7.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2823   -6.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -6.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1471   -6.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -6.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7100   -6.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874   -5.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289   -5.4393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -3.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  4 11  1  0
  1  2  2  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  4  2  0
 13 14  1  0
  4  5  1  0
 14 15  2  0
  5  6  2  0
 15 16  1  0
  6  1  1  0
 16 17  2  0
 17 12  1  0
  6  7  1  0
 15 18  1  0
  7  8  1  0
 18 19  1  0
  8  9  1  0
 18 20  2  0
  8 21  1  0
  9 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA608107

   4-[[3-(2-Amino-2-carboxyethyl)phenyl]methyl]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: 299.33

Molecular Weight (Monoisotopic): 299.1158

AlogP: 1.93

#Rotatable Bonds: 6

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: 2.12

CX Basic pKa: 9.45

CX LogP: 0.50

CX LogD: -2.48

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.29

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]

Source

Source(1):

• Scientific Literature