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

ID: ALA3950379

PubChem CID: 134147884

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)c1cccc(Cl)c1)C(=O)O

Standard InChI:  InChI=1S/C10H11ClN2O6S/c11-5-2-1-3-6(4-5)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:  UKRLHWGNMLLOIW-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   18.8318   -2.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6575   -2.9649    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2446   -2.2499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7087   -5.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9875   -5.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2768   -5.4759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9680   -4.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2467   -3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5319   -4.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2230   -3.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4236   -5.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7324   -6.2580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6758   -3.7934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3633   -2.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0802   -2.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7856   -2.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7706   -1.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0441   -1.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3417   -1.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5080   -2.9150    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
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3950379

   ---

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: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.15

CX Basic pKa: 8.56

CX LogP: -2.58

CX LogD: -5.79

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.55

Np Likeness Score: -1.22

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