3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(1-hydroxy-1-pyridin-3-yl-ethyl)-phenyl]-propionic acid

ID: ALA116970

PubChem CID: 10696378

Max Phase: Preclinical

Molecular Formula: C24H25ClN2O5S

Molecular Weight: 488.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(O)(c1cccnc1)c1cc(CCNS(=O)(=O)c2ccc(Cl)cc2)cc(CCC(=O)O)c1

Standard InChI:  InChI=1S/C24H25ClN2O5S/c1-24(30,19-3-2-11-26-16-19)20-14-17(4-9-23(28)29)13-18(15-20)10-12-27-33(31,32)22-7-5-21(25)6-8-22/h2-3,5-8,11,13-16,27,30H,4,9-10,12H2,1H3,(H,28,29)

Standard InChI Key:  PGOWTYFIKKGJRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.1375   -0.3042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -1.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292    0.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2167    0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -3.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042    0.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -3.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5625   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4375   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8542   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  2  0
  3  2  1  0
  4  1  1  0
  5  1  2  0
  6  1  2  0
  7  3  1  0
  8  1  1  0
  9 12  2  0
 10 15  1  0
 11 20  1  0
 12 18  1  0
 13 26  1  0
 14 11  2  0
 15 31  1  0
 16  4  2  0
 17  4  1  0
 18 15  2  0
 19  3  1  0
 20 22  1  0
 21 24  1  0
 22 12  1  0
 23 11  1  0
 24 17  2  0
 25 16  1  0
 26  7  2  0
 27 21  1  0
 28  8  1  0
 29  3  1  0
 30  7  1  0
 31 28  1  0
 32 33  1  0
 33 30  2  0
 21 25  2  0
  2  9  1  0
 32 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA116970

   3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(1-hydroxy-1-pyridin-3-yl-ethyl)-phenyl]-propionic acid

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: 488.99

Molecular Weight (Monoisotopic): 488.1173

AlogP: 3.53

#Rotatable Bonds: 10

Polar Surface Area: 116.59

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: 4.73

CX LogP: 2.63

CX LogD: 0.32

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.89

References

1. Dickinson RP, Dack KN, Long CJ, Steele J..  (1997)  Thromboxane modulating agents. 3. 1H-imidazol-1-ylalkyl- and 3-pyridinylalkyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists.,  40  (21): [PMID:9341919] [10.1021/jm9702793]

Source

Source(1):

• Scientific Literature