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

ID: ALA3955070

PubChem CID: 134144947

Max Phase: Preclinical

Molecular Formula: C10H7F5N2O6S

Molecular Weight: 378.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1c(F)c(F)c(F)c(F)c1F)C(=O)O

Standard InChI:  InChI=1S/C10H7F5N2O6S/c11-1-2(12)4(14)8(5(15)3(1)13)24(22,23)17-7(10(20)21)6(16)9(18)19/h6-7,17H,16H2,(H,18,19)(H,20,21)/t6-,7?/m0/s1

Standard InChI Key:  AKXRXJBXWQKMKU-PKPIPKONSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   12.6087  -20.6279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4259  -20.6279    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0173  -19.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4767  -23.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7628  -22.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0594  -23.1132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7435  -21.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0296  -21.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3221  -21.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062  -20.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1842  -22.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5001  -23.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4440  -21.4479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1245  -20.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8340  -20.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5322  -20.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5173  -19.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7983  -18.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1031  -19.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8472  -21.4204    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2472  -20.5785    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2166  -18.9437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7801  -18.1552    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.3856  -19.0037    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
 15 20  1  0
 16 21  1  0
 17 22  1  0
 18 23  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3955070

   ---

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: 378.23

Molecular Weight (Monoisotopic): 377.9945

AlogP: -0.47

#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: 1.50

CX Basic pKa: 8.63

CX LogP: -2.44

CX LogD: -6.62

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.30

Np Likeness Score: -0.57

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]

2. 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