3-(4-benzylpiperazin-1-yl)-N-(4-sulfamoylcyclohexa-2,5-dienyl)propanamide

ID: ALA1077151

PubChem CID: 46881373

Max Phase: Preclinical

Molecular Formula: C20H28N4O3S

Molecular Weight: 404.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)C1C=CC(NC(=O)CCN2CCN(Cc3ccccc3)CC2)C=C1

Standard InChI:  InChI=1S/C20H28N4O3S/c21-28(26,27)19-8-6-18(7-9-19)22-20(25)10-11-23-12-14-24(15-13-23)16-17-4-2-1-3-5-17/h1-9,18-19H,10-16H2,(H,22,25)(H2,21,26,27)

Standard InChI Key:  KCEXHFMNAPSTBL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   18.5167   -5.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3417   -5.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7519   -4.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3417   -3.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5167   -3.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1019   -4.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5769   -4.4240    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.9884   -5.1390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3583   -3.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3708   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2769   -4.4240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8634   -3.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0384   -3.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2749   -2.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6249   -2.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7999   -2.9985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3929   -2.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5715   -2.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562   -2.9954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5684   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3961   -3.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3312   -2.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9170   -3.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0936   -3.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6795   -4.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0903   -5.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9196   -5.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3300   -4.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  3  7  1  0
 13 15  1  0
  1  2  2  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  1  6  1  0
  7  9  2  0
  2  3  1  0
  7 10  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  3  4  1  0
 19 22  1  0
  6 11  1  0
 22 23  1  0
  4  5  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  5  6  1  0
 25 26  2  0
 12 13  1  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077151

   3-(4-benzylpiperazin-1-yl)-N-(4-sulfamoylcyclohexa-2,5-dien-1-yl)propanamide

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: 404.54

Molecular Weight (Monoisotopic): 404.1882

AlogP: 0.46

#Rotatable Bonds: 7

Polar Surface Area: 95.74

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.44

CX Basic pKa: 8.12

CX LogP: 0.49

CX LogD: -0.30

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -1.12

References

1. Oltulu O, Yaşar MM, Eroğlu E..  (2009)  A QSAR study on relationship between structure of sulfonamides and their carbonic anhydrase inhibitory activity using the eigenvalue (EVA) method.,  44  (9): [PMID:19303173] [10.1016/j.ejmech.2009.02.016]

Source

Source(1):

• Scientific Literature