2-(3-(phenylsulfonyl)ureido)-N-propyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide

ID: ALA574651

PubChem CID: 45112560

Max Phase: Preclinical

Molecular Formula: C20H25N3O4S2

Molecular Weight: 435.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1c(NC(=O)NS(=O)(=O)c2ccccc2)sc2c1CCCCC2

Standard InChI:  InChI=1S/C20H25N3O4S2/c1-2-13-21-18(24)17-15-11-7-4-8-12-16(15)28-19(17)22-20(25)23-29(26,27)14-9-5-3-6-10-14/h3,5-6,9-10H,2,4,7-8,11-13H2,1H3,(H,21,24)(H2,22,23,25)

Standard InChI Key:  OUDXNOQMKPCNTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    1.7400  -18.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846  -18.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5472  -19.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0561  -20.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821  -20.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2239  -18.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043  -19.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211  -19.5315    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455  -18.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296  -18.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697  -18.7749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7856  -19.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6106  -19.4834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765  -20.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0265  -20.1959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8515  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2656  -20.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898  -20.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4997  -20.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0794  -19.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566  -19.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3245  -20.6359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4333  -20.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083  -17.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119  -16.9813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835  -17.0181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799  -17.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550  -17.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514  -17.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  1  3  1  0
 13 15  1  0
  1  2  1  0
 15 16  1  0
  3  4  1  0
 16 17  2  0
  2  6  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
  8  9  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 21 16  1  0
 10  6  1  0
 15 22  2  0
  7  5  1  0
 15 23  2  0
  9 11  1  0
 10 24  1  0
  4  5  1  0
 24 25  2  0
 11 12  1  0
 24 26  1  0
  6  7  2  0
 26 27  1  0
 12 13  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA574651

   2-(benzenesulfonylcarbamoylamino)-N-propyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide

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: 435.57

Molecular Weight (Monoisotopic): 435.1286

AlogP: 3.67

#Rotatable Bonds: 6

Polar Surface Area: 104.37

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 5.05

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.93

References

1. El-Sherbeny MA, Abdel-Aziz AA, Ahmed MA..  (2010)  Synthesis and antitumor evaluation of novel diarylsulfonylurea derivatives: molecular modeling applications.,  45  (2): [PMID:19939520] [10.1016/j.ejmech.2009.11.014]

Source

Source(1):

• Scientific Literature