4-Chloro-N-(5-((4-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)methyl)-1,2,3,4-tetrahydro naphthalen-2-yl)benzenesulfonamide

ID: ALA3354613

PubChem CID: 117631017

Max Phase: Preclinical

Molecular Formula: C23H24ClNO4S

Molecular Weight: 445.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(O)CC(Cc2cccc3c2CCC(NS(=O)(=O)c2ccc(Cl)cc2)C3)C1=O

Standard InChI:  InChI=1S/C23H24ClNO4S/c1-14-22(26)13-17(23(14)27)11-15-3-2-4-16-12-19(7-10-21(15)16)25-30(28,29)20-8-5-18(24)6-9-20/h2-6,8-9,17,19,25-26H,7,10-13H2,1H3

Standard InChI Key:  QIWVMARQEAOIQU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.2298   -7.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8689   -8.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0689  -10.3684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7801   -9.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5393   -8.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6545   -8.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5997   -9.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2150   -8.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9957   -6.0291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765   -5.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8658   -4.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8317   -6.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -4.8081    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1606   -6.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073   -7.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8719   -6.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556   -5.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -7.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2862   -6.4438    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4194   -6.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5415   -7.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4194   -7.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8326   -7.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1273   -6.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8775   -7.1495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6946   -7.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5749   -6.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8320   -8.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
  8  5  1  0
  7  2  2  0
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  9 21  1  0
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 26 22  1  0
 24 20  1  0
 11 19  2  0
 14 26  1  0
 23 12  1  0
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 25 23  2  0
 19 15  1  0
 21 28  2  0
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 21 29  1  0
 12 14  2  0
 20 25  1  0
 10 11  1  0
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 25 30  1  0
 30  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3354613

   4-chloro-N-[5-[(2-hydroxy-3-methyl-4-oxocyclopent-2-en-1-yl)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]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: 445.97

Molecular Weight (Monoisotopic): 445.1115

AlogP: 4.14

#Rotatable Bonds: 5

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.56

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 4.69

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: -0.37

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