(3S)-2-([1,1'-Biphenyl]-4-sulfonamido)-3-aminoaspartic Acid

ID: ALA3939524

PubChem CID: 134149427

Max Phase: Preclinical

Molecular Formula: C16H16N2O6S

Molecular Weight: 364.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1ccc(-c2ccccc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C16H16N2O6S/c17-13(15(19)20)14(16(21)22)18-25(23,24)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13-14,18H,17H2,(H,19,20)(H,21,22)/t13-,14?/m0/s1

Standard InChI Key:  PDTYFUFTPPYALH-LSLKUGRBSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   12.0905   -3.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9163   -3.8119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.5034   -3.0968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9676   -6.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2463   -5.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5354   -6.3233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2267   -5.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5054   -4.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7904   -5.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4817   -3.8513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6827   -5.8526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9914   -7.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9346   -4.6405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6223   -3.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3393   -3.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0447   -3.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0297   -2.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3032   -2.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6007   -2.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7319   -2.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4555   -2.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1617   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1456   -1.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4172   -0.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7140   -1.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  4 11  2  0
  4 12  1  0
  7 13  1  0
 13  2  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3939524

   ---

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: 364.38

Molecular Weight (Monoisotopic): 364.0729

AlogP: 0.50

#Rotatable Bonds: 7

Polar Surface Area: 146.79

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.36

CX Basic pKa: 8.60

CX LogP: -1.53

CX LogD: -4.71

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -0.63

References

1. Hansen JC, Bjørn-Yoshimoto WE, Bisballe N, Nielsen B, Jensen AA, Bunch L..  (2016)  β-Sulfonamido Functionalized Aspartate Analogues as Excitatory Amino Acid Transporter Inhibitors: Distinct Subtype Selectivity Profiles Arising from Subtle Structural Differences.,  59  (19): [PMID:27636002] [10.1021/acs.jmedchem.6b01066]

Source

Source(1):

• Scientific Literature