3-[3-(2-Benzenesulfonylamino-ethyl)-5-imidazol-1-ylmethyl-phenyl]-propionic acid

ID: ALA117752

PubChem CID: 10835548

Max Phase: Preclinical

Molecular Formula: C21H23N3O4S

Molecular Weight: 413.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)c2ccccc2)cc(Cn2ccnc2)c1

Standard InChI:  InChI=1S/C21H23N3O4S/c25-21(26)7-6-17-12-18(14-19(13-17)15-24-11-10-22-16-24)8-9-23-29(27,28)20-4-2-1-3-5-20/h1-5,10-14,16,23H,6-9,15H2,(H,25,26)

Standard InChI Key:  DOUQUVSMHBZKHU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.6875    0.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792    1.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    2.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833    0.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    1.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1667    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -2.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    2.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333    2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  3 13  1  0
  4  3  1  0
  5  1  2  0
  6  1  2  0
  7  1  1  0
  8 18  2  0
  9  1  1  0
 10 20  1  0
 11 12  2  0
 12  3  1  0
 13  8  1  0
 14 10  2  0
 15 19  1  0
 16 24  1  0
 17 15  2  0
 18 16  1  0
 19 16  2  0
 20 21  1  0
 21 15  1  0
 22 10  1  0
 23  9  1  0
 24 23  1  0
 25  7  2  0
 26  7  1  0
 27 25  1  0
 28 26  2  0
 29 28  1  0
 27 29  2  0
 17  8  1  0
 11  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA117752

   3-[3-(2-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: 413.50

Molecular Weight (Monoisotopic): 413.1409

AlogP: 2.47

#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: 1.93

CX LogD: 0.94

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.19

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