(RS)-2-Amino-3-(5,6-dichloro-3'-(1H-tetrazol-5-yl)-biphenyl-3-yl)propanoic acid

ID: ALA594617

PubChem CID: 46226995

Max Phase: Preclinical

Molecular Formula: C16H13Cl2N5O2

Molecular Weight: 378.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1cc(Cl)c(Cl)c(-c2cccc(-c3nnn[nH]3)c2)c1)C(=O)O

Standard InChI:  InChI=1S/C16H13Cl2N5O2/c17-12-5-8(6-13(19)16(24)25)4-11(14(12)18)9-2-1-3-10(7-9)15-20-22-23-21-15/h1-5,7,13H,6,19H2,(H,24,25)(H,20,21,22,23)

Standard InChI Key:  LRMSVXGHFASGAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.0265  -22.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7811  -22.3430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3289  -21.7272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9156  -21.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490  -21.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469  -22.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625  -22.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772  -22.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725  -21.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583  -20.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922  -22.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8926  -23.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032  -23.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188  -23.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3113  -22.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6015  -22.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583  -19.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7419  -19.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420  -18.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307  -18.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4624  -23.2560    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0317  -22.4348    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1101  -21.1936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -19.9584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568  -18.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
  7 21  1  0
  6 22  1  0
  1 15  1  0
  1  2  2  0
  2  3  1  0
 18 24  1  0
  4 23  1  0
 23  1  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA594617

   2-amino-3-[3,4-dichloro-5-[3-(2H-tetrazol-5-yl)phenyl]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: 378.22

Molecular Weight (Monoisotopic): 377.0446

AlogP: 2.79

#Rotatable Bonds: 5

Polar Surface Area: 117.78

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.05

CX Basic pKa: 9.42

CX LogP: 0.90

CX LogD: -0.65

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -0.69

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