(2S)-3-(Naphthalene-1-sulfonamido)aspartic Acid

ID: ALA3967211

PubChem CID: 134149841

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)c1cccc2ccccc12)C(=O)O

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

Standard InChI Key:  QTKQWWVIXJJZGN-PXYINDEMSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   12.8331  -21.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6624  -21.1806    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.2478  -20.4624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7140  -23.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9896  -23.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2757  -23.7027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9699  -22.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2456  -22.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5275  -22.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2217  -21.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4321  -23.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7378  -24.4882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6808  -22.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3715  -20.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7848  -19.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0553  -19.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3498  -19.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7999  -20.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0915  -21.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1043  -21.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8248  -22.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5340  -21.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5176  -21.1267    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 19  2  0
 18 15  2  0
 15 16  1  0
 16 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3967211

   ---

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: 2.53

CX Basic pKa: 8.59

CX LogP: -2.14

CX LogD: -5.34

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.67

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