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

ID: ALA3911432

PubChem CID: 134132565

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-JGVFFNPUSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.3154  -20.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326  -20.1285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240  -19.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833  -22.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4695  -22.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661  -22.6138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502  -21.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7363  -20.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288  -21.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128  -20.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909  -22.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2068  -23.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507  -20.9485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312  -19.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407  -20.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389  -19.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240  -18.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5050  -18.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8098  -18.8955    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  6
 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:

   

   ALA3911432

   ---

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