N-(4-benzyloxyphenyl)-2-(2-p-tolylethenesulfonylamino)acetamide

ID: ALA4067732

PubChem CID: 26500226

Max Phase: Preclinical

Molecular Formula: C24H24N2O4S

Molecular Weight: 436.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(/C=C/S(=O)(=O)NCC(=O)Nc2ccc(OCc3ccccc3)cc2)cc1

Standard InChI:  InChI=1S/C24H24N2O4S/c1-19-7-9-20(10-8-19)15-16-31(28,29)25-17-24(27)26-22-11-13-23(14-12-22)30-18-21-5-3-2-4-6-21/h2-16,25H,17-18H2,1H3,(H,26,27)/b16-15+

Standard InChI Key:  WADQGOCHLKZPTC-FOCLMDBBSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.0102   -8.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6058   -7.7509    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968   -8.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0249   -8.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0249   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3158   -8.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7299   -8.9767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3158   -7.3423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8863   -7.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8642   -6.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1443   -6.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4487   -6.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066   -5.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1200   -5.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7288   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4023   -4.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867   -4.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4390   -8.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1439   -8.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8530   -8.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8530   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1439   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4389   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5621   -7.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2671   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9761   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6852   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3902   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3902   -6.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6852   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9761   -6.5251    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
  4  6  2  0
  4  7  1  0
  9 10  2  0
  2  9  1  0
 11 12  1  0
 11 14  2  0
 12 15  2  0
 13 15  1  0
 13 16  2  0
 14 16  1  0
 13 17  1  0
 10 11  1  0
  8  2  1  0
  5  8  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 24 25  1  0
 21 24  1  0
  7 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4067732

   2-[[(E)-2-(4-methylphenyl)ethenyl]sulfonylamino]-N-(4-phenylmethoxyphenyl)acetamide

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: 436.53

Molecular Weight (Monoisotopic): 436.1457

AlogP: 4.10

#Rotatable Bonds: 9

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.95

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.36

References

1. Mori H, Wada R, Takahara S, Horino Y, Izumi H, Ishimoto T, Yoshida T, Mizuguchi M, Obita T, Gouda H, Hirono S, Toyooka N..  (2017)  A novel serine racemase inhibitor suppresses neuronal over-activation in vivo.,  25  (14): [PMID:28533113] [10.1016/j.bmc.2017.05.011]

2.  (2014)  Serine racemase inhibitor, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data