3-{3-[2-(Piperidine-1-sulfonylamino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

ID: ALA119035

PubChem CID: 11796949

Max Phase: Preclinical

Molecular Formula: C22H29N3O4S

Molecular Weight: 431.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)N2CCCCC2)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C22H29N3O4S/c26-22(27)7-6-18-13-19(15-21(14-18)16-20-5-4-9-23-17-20)8-10-24-30(28,29)25-11-2-1-3-12-25/h4-5,9,13-15,17,24H,1-3,6-8,10-12,16H2,(H,26,27)

Standard InChI Key:  YFYJSJBIRHAOGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.7625   -0.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -0.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125   -0.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -4.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6000   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8750   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -1.7042    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 23  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  2  1  0
 22  2  1  0
 23 19  2  0
 24 20  1  0
 25 29  1  0
 26 19  1  0
 27 22  1  0
 28 21  1  0
 29 26  2  0
 30 27  1  0
 30 28  1  0
  5 12  2  0
 25  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA119035

   3-{3-[2-(Piperidine-1-sulfonylamino)-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: 431.56

Molecular Weight (Monoisotopic): 431.1879

AlogP: 2.55

#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: 1.40

CX LogD: -0.35

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: -0.80

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