2-(6-(4-chlorophenylsulfonamido)-5,6,7,8-tetrahydronaphthalen-1-yl)acetic acid

ID: ALA3335473

PubChem CID: 118714499

Max Phase: Preclinical

Molecular Formula: C18H18ClNO4S

Molecular Weight: 379.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1cccc2c1CCC(NS(=O)(=O)c1ccc(Cl)cc1)C2

Standard InChI:  InChI=1S/C18H18ClNO4S/c19-14-4-7-16(8-5-14)25(23,24)20-15-6-9-17-12(10-15)2-1-3-13(17)11-18(21)22/h1-5,7-8,15,20H,6,9-11H2,(H,21,22)

Standard InChI Key:  XMIGWECSZMISCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.9014   -1.8696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.1639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -2.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232   -1.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216   -1.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0258   -2.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7321   -1.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297   -1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249   -0.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -0.7532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883   -0.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7899    0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0818    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3743    0.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -0.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3417    0.4644    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0251   -3.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7325   -3.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7325   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4412   -3.2018    0.0000 O   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  7  1  0
  5  6  1  0
  6  9  1  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335473

   ---

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: 379.87

Molecular Weight (Monoisotopic): 379.0645

AlogP: 2.80

#Rotatable Bonds: 5

Polar Surface Area: 83.47

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 0.31

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.84

Np Likeness Score: -0.78

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