(2S)-3-((3-(Trifluoromethyl)phenyl)sulfonamido)aspartic Acid

ID: ALA3894651

PubChem CID: 134136786

Max Phase: Preclinical

Molecular Formula: C11H11F3N2O6S

Molecular Weight: 356.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1cccc(C(F)(F)F)c1)C(=O)O

Standard InChI:  InChI=1S/C11H11F3N2O6S/c12-11(13,14)5-2-1-3-6(4-5)23(21,22)16-8(10(19)20)7(15)9(17)18/h1-4,7-8,16H,15H2,(H,17,18)(H,19,20)/t7-,8?/m0/s1

Standard InChI Key:  FATMQFBYVIKULP-JAMMHHFISA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.7762   -9.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -9.3105    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890   -8.5955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531  -11.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9319  -11.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213  -11.8212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9124  -10.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913  -10.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4764  -10.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -9.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678  -11.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6768  -12.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201  -10.1389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075   -8.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0243   -9.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297   -8.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146   -8.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883   -7.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2859   -8.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513   -9.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1086   -9.6259    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045  -10.1113    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2520   -8.9409    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
 20 21  1  0
 20 22  1  0
 20 23  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3894651

   ---

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: 356.28

Molecular Weight (Monoisotopic): 356.0290

AlogP: -0.15

#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: 2.42

CX Basic pKa: 8.60

CX LogP: -2.28

CX LogD: -5.48

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: -1.23

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