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

ID: ALA115636

PubChem CID: 10810477

Max Phase: Preclinical

Molecular Formula: C19H25N3O4S

Molecular Weight: 391.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)S(=O)(=O)NCCc1cc(CCC(=O)O)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C19H25N3O4S/c1-22(2)27(25,26)21-9-7-16-10-15(5-6-19(23)24)11-18(12-16)13-17-4-3-8-20-14-17/h3-4,8,10-12,14,21H,5-7,9,13H2,1-2H3,(H,23,24)

Standard InChI Key:  KYHWNHYXJBSHSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.1250   -4.6792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -5.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -3.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -4.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2500   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -8.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -8.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5417   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -4.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2375   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5167   -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 27  1  0
 26 19  1  0
 27 26  2  0
  5 12  2  0
 25  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA115636

   3-{3-[2-(Sulfo-[dimethylamine]-amino)-ethyl]-5-pyridin-3-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: 391.49

Molecular Weight (Monoisotopic): 391.1566

AlogP: 1.63

#Rotatable Bonds: 10

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: 0.55

CX LogD: -1.20

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.67

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