3-{3-[2-(sulfo-[diethylamine]-amino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

ID: ALA115806

PubChem CID: 11796350

Max Phase: Preclinical

Molecular Formula: C21H29N3O4S

Molecular Weight: 419.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)S(=O)(=O)NCCc1cc(CCC(=O)O)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C21H29N3O4S/c1-3-24(4-2)29(27,28)23-11-9-18-12-17(7-8-21(25)26)13-20(14-18)15-19-6-5-10-22-16-19/h5-6,10,12-14,16,23H,3-4,7-9,11,15H2,1-2H3,(H,25,26)

Standard InChI Key:  QSVUPNAXKJMPOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    3.4792   -4.6792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -5.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -3.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -8.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -8.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -6.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8750   -6.0417    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 13  1  0
  6  1  1  0
  7 16  1  0
  8 21  1  0
  9  7  2  0
 10 15  2  0
 11 24  1  0
 12 10  1  0
 13 11  2  0
 14  5  1  0
 15 11  1  0
 16 17  1  0
 17 10  1  0
 18  7  1  0
 19 14  1  0
 20  6  1  0
 21 19  2  0
 22  2  1  0
 23  2  1  0
 24 20  1  0
 25 29  1  0
 26 19  1  0
 27 22  1  0
 28 23  1  0
 29 26  2  0
  5 12  2  0
 25  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA115806

   3-[3-[2-(Diethylsulfamoylamino)ethyl]-5-(pyridin-3-ylmethyl)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: 419.55

Molecular Weight (Monoisotopic): 419.1879

AlogP: 2.41

#Rotatable Bonds: 12

Polar Surface Area: 99.60

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: 5.43

CX LogP: 1.26

CX LogD: -0.49

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -0.75

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