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

ID: ALA3938810

PubChem CID: 134149212

Max Phase: Preclinical

Molecular Formula: C11H14N2O6S

Molecular Weight: 302.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1S(=O)(=O)NC(C(=O)O)[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C11H14N2O6S/c1-6-4-2-3-5-7(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:  COGJSNZLBJCRKR-IENPIDJESA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   18.6066   -9.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4323   -9.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0194   -9.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4836  -12.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7623  -11.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0516  -12.3689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7428  -11.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0215  -10.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3067  -11.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9978   -9.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1984  -11.8982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5072  -13.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4506  -10.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1381   -9.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8550   -9.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5604   -9.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5453   -8.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8190   -8.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1165   -8.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8683  -10.6587    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
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3938810

   ---

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: 2.34

CX Basic pKa: 8.61

CX LogP: -2.67

CX LogD: -5.85

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: -0.93

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