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

ID: ALA3920012

PubChem CID: 134139672

Max Phase: Preclinical

Molecular Formula: C10H11ClN2O6S

Molecular Weight: 322.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1ccccc1Cl)C(=O)O

Standard InChI:  InChI=1S/C10H11ClN2O6S/c11-5-3-1-2-4-6(5)20(18,19)13-8(10(16)17)7(12)9(14)15/h1-4,7-8,13H,12H2,(H,14,15)(H,16,17)/t7-,8?/m0/s1

Standard InChI Key:  MKWFCJWXSLFYBE-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   14.3222   -9.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1478   -9.7900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.7350   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1991  -12.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4780  -11.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7673  -12.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4584  -11.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7373  -10.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0224  -11.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7135   -9.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9139  -11.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2228  -13.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1661  -10.6185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8536   -9.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5704   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2756   -9.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2606   -8.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5343   -8.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8320   -8.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5837  -10.5906    0.0000 Cl  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
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3920012

   ---

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: 322.73

Molecular Weight (Monoisotopic): 322.0026

AlogP: -0.52

#Rotatable Bonds: 6

Polar Surface Area: 146.79

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.15

CX Basic pKa: 8.48

CX LogP: -2.58

CX LogD: -5.79

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.55

Np Likeness Score: -1.09

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