3-{3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-imidazol-1-ylmethyl-phenyl}-propionic acid

ID: ALA418852

PubChem CID: 10742084

Max Phase: Preclinical

Molecular Formula: C21H22ClN3O4S

Molecular Weight: 447.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)c2ccc(Cl)cc2)cc(Cn2ccnc2)c1

Standard InChI:  InChI=1S/C21H22ClN3O4S/c22-19-2-4-20(5-3-19)30(28,29)24-8-7-17-11-16(1-6-21(26)27)12-18(13-17)14-25-10-9-23-15-25/h2-5,9-13,15,24H,1,6-8,14H2,(H,26,27)

Standard InChI Key:  KIDWBDAXUAZZFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.6875    1.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792    1.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    2.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    1.7708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292    2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9917   -1.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4667    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -2.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458    3.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3 13  1  0
  4  1  1  0
  5  3  1  0
  6  1  2  0
  7  1  2  0
  8 20  2  0
  9  1  1  0
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 18  4  1  0
 19 15  2  0
 20 16  1  0
 21 16  2  0
 22 24  1  0
 23 26  1  0
 24 15  1  0
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 26 18  2  0
 27 17  1  0
 28 23  1  0
 29  9  1  0
 30 29  1  0
 27 23  2  0
 19  8  1  0
 11  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA418852

   3-{3-[2-(4-Chloro-benzenesulfonylamino)-ethyl]-5-imidazol-1-ylmethyl-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: 447.94

Molecular Weight (Monoisotopic): 447.1020

AlogP: 3.12

#Rotatable Bonds: 10

Polar Surface Area: 101.29

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.04

CX Basic pKa: 6.47

CX LogP: 2.54

CX LogD: 1.55

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.31

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