4-Chloro-N-(3-((3-cyclohexyl-4-hydroxy-2-oxocyclopent-3-en-1-yl)methyl)phenethyl)benzenesulfonamide

ID: ALA3335483

PubChem CID: 71138378

Max Phase: Preclinical

Molecular Formula: C26H30ClNO4S

Molecular Weight: 488.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(C2CCCCC2)=C(O)CC1Cc1cccc(CCNS(=O)(=O)c2ccc(Cl)cc2)c1

Standard InChI:  InChI=1S/C26H30ClNO4S/c27-22-9-11-23(12-10-22)33(31,32)28-14-13-18-5-4-6-19(15-18)16-21-17-24(29)25(26(21)30)20-7-2-1-3-8-20/h4-6,9-12,15,20-21,28-29H,1-3,7-8,13-14,16-17H2

Standard InChI Key:  XHQGHWHPDAWUIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    7.1484   -6.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439   -6.1743    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3349   -6.8775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1595   -6.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8648   -5.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5701   -6.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5685   -6.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2727   -7.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9790   -6.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9767   -6.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2719   -5.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4506   -5.7637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0352   -5.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0368   -4.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287   -4.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -4.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263   -5.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -6.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9118   -4.5504    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2758   -8.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9851   -8.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0744   -9.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8744   -9.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2803   -8.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7311   -8.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8968   -7.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2096  -10.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0927   -8.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5724   -9.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3814   -9.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7149   -8.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2330   -7.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4176   -8.0445    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
  6  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
 12  2  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 25 26  2  0
 23 27  1  0
 24 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335483

   4-chloro-N-[2-[3-[(3-cyclohexyl-2-hydroxy-4-oxocyclopent-2-en-1-yl)methyl]phenyl]ethyl]benzenesulfonamide

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: 488.05

Molecular Weight (Monoisotopic): 487.1584

AlogP: 5.38

#Rotatable Bonds: 8

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.61

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.75

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -0.44

References

1. Wang X, Liu L, Huang L, Herbst-Robinson K, Cornec AS, James MJ, Sugiyama S, Bassetto M, Brancale A, Trojanowski JQ, Lee VM, Smith AB, Brunden KR, Ballatore C..  (2014)  Potent, long-acting cyclopentane-1,3-Dione thromboxane (A2)-receptor antagonists.,  5  (9): [PMID:25221659] [10.1021/ml5002085]

Source

Source(1):

• Scientific Literature