(3S)-2-((4-Acetylphenyl)sulfonamido)-3-aminoaspartic Acid

ID: ALA3920488

PubChem CID: 134140412

Max Phase: Preclinical

Molecular Formula: C12H14N2O7S

Molecular Weight: 330.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(S(=O)(=O)NC(C(=O)O)[C@H](N)C(=O)O)cc1

Standard InChI:  InChI=1S/C12H14N2O7S/c1-6(15)7-2-4-8(5-3-7)22(20,21)14-10(12(18)19)9(13)11(16)17/h2-5,9-10,14H,13H2,1H3,(H,16,17)(H,18,19)/t9-,10?/m0/s1

Standard InChI Key:  XMYKJOBTTGFNKX-RGURZIINSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    6.7434   -3.5883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5685   -3.5883    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1560   -2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6198   -6.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8990   -5.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887   -6.0980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8794   -4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1586   -4.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4440   -4.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1349   -3.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3343   -5.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6435   -6.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -4.4165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2740   -3.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9905   -3.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6954   -3.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6804   -2.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9544   -1.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2524   -2.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3861   -1.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1089   -2.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3696   -1.0623    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  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  2  0
 20 22  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3920488

   ---

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: 330.32

Molecular Weight (Monoisotopic): 330.0522

AlogP: -0.97

#Rotatable Bonds: 7

Polar Surface Area: 163.86

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.98

CX Basic pKa: 8.40

CX LogP: -3.58

CX LogD: -6.86

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.46

Np Likeness Score: -0.69

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