(2S)-3-((4-Methylphenyl)sulfonamido)aspartic Acid

ID: ALA3974720

PubChem CID: 134153858

Max Phase: Preclinical

Molecular Formula: C11H14N2O6S

Molecular Weight: 302.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NC(C(=O)O)[C@H](N)C(=O)O)cc1

Standard InChI:  InChI=1S/C11H14N2O6S/c1-6-2-4-7(5-3-6)20(18,19)13-9(11(16)17)8(12)10(14)15/h2-5,8-9,13H,12H2,1H3,(H,14,15)(H,16,17)/t8-,9?/m0/s1

Standard InChI Key:  QECYIKYYAOOLLH-IENPIDJESA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   21.8967  -20.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7224  -20.4998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.3096  -19.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7736  -22.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0524  -22.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3418  -23.0108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0329  -21.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3116  -21.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5968  -21.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2880  -20.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4886  -22.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7974  -23.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7407  -21.3283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4283  -20.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1451  -20.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8506  -20.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8355  -19.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1090  -18.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4066  -19.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5420  -18.7982    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
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974720

   ---

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: 302.31

Molecular Weight (Monoisotopic): 302.0573

AlogP: -0.86

#Rotatable Bonds: 6

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: 2.22

CX Basic pKa: 8.61

CX LogP: -2.70

CX LogD: -5.86

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: -0.82

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