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

ID: ALA3975687

PubChem CID: 134152143

Max Phase: Preclinical

Molecular Formula: C10H11BrN2O6S

Molecular Weight: 367.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H11BrN2O6S/c11-5-1-3-6(4-2-5)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:  NPZGPHKBQHVBNJ-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   17.1158  -20.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9414  -20.7391    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5286  -20.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9926  -23.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2715  -22.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5609  -23.2498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2520  -21.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5308  -21.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160  -22.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5071  -20.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7075  -22.7791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0164  -24.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9597  -21.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6471  -20.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3639  -20.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0693  -20.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0542  -19.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3279  -19.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6255  -19.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7607  -19.0377    0.0000 Br  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:

   

   ALA3975687

   ---

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: 367.18

Molecular Weight (Monoisotopic): 365.9521

AlogP: -0.41

#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: 1.65

CX Basic pKa: 8.57

CX LogP: -2.36

CX LogD: -5.65

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