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

ID: ALA326356

PubChem CID: 10502084

Max Phase: Preclinical

Molecular Formula: C21H27N3O4S

Molecular Weight: 417.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1cc(CCNS(=O)(=O)N2CCCC2)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C21H27N3O4S/c25-21(26)6-5-17-12-18(7-9-23-29(27,28)24-10-1-2-11-24)14-20(13-17)15-19-4-3-8-22-16-19/h3-4,8,12-14,16,23H,1-2,5-7,9-11,15H2,(H,25,26)

Standard InChI Key:  BSTJPYNZDQCBNL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.4167   -0.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4000    1.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292    0.9958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375    0.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -3.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4292    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8125   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6208   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -0.7792    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
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 13 11  2  0
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 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
 27 28  1  0
  5 12  2  0
 25  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326356

   3-{3-Pyridin-3-ylmethyl-5-[2-(pyrrolidine-1-sulfonylamino)-ethyl]-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: 417.53

Molecular Weight (Monoisotopic): 417.1722

AlogP: 2.16

#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: 0.96

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -0.81

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