3-[3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-(4-methoxy-benzyl)-phenyl]-propionic acid

ID: ALA417742

PubChem CID: 44305347

Max Phase: Preclinical

Molecular Formula: C25H26ClNO5S

Molecular Weight: 488.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2cc(CCNS(=O)(=O)c3ccc(Cl)cc3)cc(CCC(=O)O)c2)cc1

Standard InChI:  InChI=1S/C25H26ClNO5S/c1-32-23-7-2-18(3-8-23)14-21-16-19(4-11-25(28)29)15-20(17-21)12-13-27-33(30,31)24-9-5-22(26)6-10-24/h2-3,5-10,15-17,27H,4,11-14H2,1H3,(H,28,29)

Standard InChI Key:  QKQMESPLMZGCNX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.3708   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3458   -1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -0.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -3.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3417   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -3.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250    0.4583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -0.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -1.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  2  0
  5 14  2  0
  6  1  1  0
  7 17  1  0
  8  7  2  0
  9 16  1  0
 10 32  1  0
 11  2  1  0
 12  2  2  0
 13  9  2  0
 14 10  1  0
 15  5  1  0
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 17 21  1  0
 18 15  1  0
 19 23  2  0
 20 29  1  0
 21  9  1  0
 22  7  1  0
 23 12  1  0
 24 11  2  0
 25 19  1  0
 26  6  1  0
 27 18  2  0
 28 18  1  0
 29 28  2  0
 30 27  1  0
 31 20  1  0
 32 26  1  0
 33 31  1  0
 19 24  1  0
  5 13  1  0
 20 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA417742

   3-[3-[2-[(4-Chlorophenyl)sulfonylamino]ethyl]-5-[(4-methoxyphenyl)methyl]phenyl]propanoic 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: 488.01

Molecular Weight (Monoisotopic): 487.1220

AlogP: 4.48

#Rotatable Bonds: 11

Polar Surface Area: 92.70

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.23

CX Basic pKa: ┄

CX LogP: 5.44

CX LogD: 2.42

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -0.66

References

1. Dack KN, Dickinson RP, Long CJ, Steele J..  (1998)  Thromboxane modulating agents. 4. Design and synthesis of 3-(2-[[(4-chlorophenyl)sulfonyl]-amino]ethyl)benzenepropanoic acid derivatives as potent thromboxane receptor antagonists.,  8  (16): [PMID:9873486] [10.1016/s0960-894x(98)00242-x]

Source

Source(1):

• Scientific Literature