(2S,3S)-3-(Phenylsulfonamido)aspartic Acid

ID: ALA3937517

PubChem CID: 134149488

Max Phase: Preclinical

Molecular Formula: C10H12N2O6S

Molecular Weight: 288.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)[C@H](NS(=O)(=O)c1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C10H12N2O6S/c11-7(9(13)14)8(10(15)16)12-19(17,18)6-4-2-1-3-5-6/h1-5,7-8,12H,11H2,(H,13,14)(H,15,16)/t7-,8-/m0/s1

Standard InChI Key:  ZHWUOFGFENMPFS-YUMQZZPRSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    7.2928  -20.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1100  -20.5619    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7014  -19.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1608  -23.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4470  -22.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7435  -23.0471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4276  -21.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7138  -21.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062  -21.8409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903  -20.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8683  -22.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1843  -23.8212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1281  -21.3819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8086  -20.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181  -20.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2163  -20.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2014  -19.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4825  -18.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7873  -19.3289    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  1
 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
M  END

Alternative Forms

1. Parent:

   

   ALA3937517

   ---

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: 288.28

Molecular Weight (Monoisotopic): 288.0416

AlogP: -1.17

#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: 2.20

CX Basic pKa: 8.60

CX LogP: -3.24

CX LogD: -6.38

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.52

Np Likeness Score: -0.76

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