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

ID: ALA3983719

PubChem CID: 134157558

Max Phase: Preclinical

Molecular Formula: C10H11FN2O6S

Molecular Weight: 306.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H11FN2O6S/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:  SHOWNKVGAYTRRR-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   12.1833  -20.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0089  -20.6765    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.5961  -19.9616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0601  -23.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3390  -22.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284  -23.1873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3194  -21.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5983  -21.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8835  -21.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5745  -20.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7750  -22.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0838  -23.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0272  -21.5049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7146  -20.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4314  -20.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1368  -20.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1217  -19.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953  -19.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6930  -19.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8282  -18.9752    0.0000 F   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:

   

   ALA3983719

   ---

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: 306.27

Molecular Weight (Monoisotopic): 306.0322

AlogP: -1.03

#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: 2.12

CX Basic pKa: 8.58

CX LogP: -3.04

CX LogD: -6.25

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: -1.07

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