(2S)-3-((3-Carboxyphenyl)sulfonamido)aspartic Acid

ID: ALA3947455

PubChem CID: 134147363

Max Phase: Preclinical

Molecular Formula: C11H12N2O8S

Molecular Weight: 332.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1cccc(C(=O)O)c1)C(=O)O

Standard InChI:  InChI=1S/C11H12N2O8S/c12-7(10(16)17)8(11(18)19)13-22(20,21)6-3-1-2-5(4-6)9(14)15/h1-4,7-8,13H,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8?/m0/s1

Standard InChI Key:  JGIPPEMTFCVDFK-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    7.7720   -9.5314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5975   -9.5314    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1847   -8.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6488  -12.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9277  -11.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171  -12.0422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9081  -10.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1870  -10.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721  -10.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1632   -9.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636  -11.5715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725  -12.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6158  -10.3599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3033   -9.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0201   -9.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7253   -9.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7103   -8.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9840   -7.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2817   -8.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4489   -9.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4640  -10.3065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1561   -9.0552    0.0000 O   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  1  0
 20 22  2  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3947455

   ---

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: 332.29

Molecular Weight (Monoisotopic): 332.0314

AlogP: -1.47

#Rotatable Bonds: 7

Polar Surface Area: 184.09

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.86

CX Basic pKa: 8.60

CX LogP: -3.47

CX LogD: -10.04

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -0.84

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