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

ID: ALA3928498

PubChem CID: 134141720

Max Phase: Preclinical

Molecular Formula: C14H14N2O6S

Molecular Weight: 338.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C(=O)O)C(NS(=O)(=O)c1ccc2ccccc2c1)C(=O)O

Standard InChI:  InChI=1S/C14H14N2O6S/c15-11(13(17)18)12(14(19)20)16-23(21,22)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11-12,16H,15H2,(H,17,18)(H,19,20)/t11-,12?/m0/s1

Standard InChI Key:  PSIIUSMBTVCZCJ-PXYINDEMSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   18.7498  -20.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5785  -20.9721    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.1641  -20.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6300  -23.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9061  -23.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1928  -23.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8865  -22.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1626  -21.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4451  -22.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1388  -21.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3474  -23.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6537  -24.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5968  -21.8037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2869  -20.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0064  -20.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9702  -19.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2652  -19.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6993  -19.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7103  -20.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4295  -20.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1380  -20.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1229  -19.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4032  -19.2707    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 19  1  0
 18 16  1  0
 16 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3928498

   ---

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: 338.34

Molecular Weight (Monoisotopic): 338.0573

AlogP: -0.02

#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: 2.41

CX Basic pKa: 8.60

CX LogP: -2.16

CX LogD: -5.36

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.78

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