US9085572, 50

ID: ALA3683788

PubChem CID: 59186972

Max Phase: Preclinical

Molecular Formula: C20H18ClN7O2

Molecular Weight: 423.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCn1cc(Cl)cn1)NCc1ccnc(-n2[nH]cc(-c3cccnc3)c2=O)c1

Standard InChI:  InChI=1S/C20H18ClN7O2/c21-16-11-25-27(13-16)7-4-19(29)24-9-14-3-6-23-18(8-14)28-20(30)17(12-26-28)15-2-1-5-22-10-15/h1-3,5-6,8,10-13,26H,4,7,9H2,(H,24,29)

Standard InChI Key:  DMTRRNGKQDUYPV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.7206  -10.7639    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -9.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9293   -9.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3978   -8.3758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343   -2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2010   -3.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1955    0.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4458   -1.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4106   -2.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8868   -2.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3943   -1.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4256   -0.1623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9494   -0.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707   -8.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 22 23  2  0
 21 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  5 30  1  0
 30  2  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3683788

   3-(4-chloropyrazol-1-yl)-N-[[2-(3-oxo-4-pyridin-3-yl-1H-pyrazol-2-yl)pyridin-4-yl]methyl]propanamide

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: 423.86

Molecular Weight (Monoisotopic): 423.1211

AlogP: 2.18

#Rotatable Bonds: 7

Polar Surface Area: 110.49

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.93

CX Basic pKa: 4.45

CX LogP: 0.65

CX LogD: -0.25

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -1.91

References

1.  (2015)  4-(pyridin-3-yl)-2(pyridin-2yl)-1,2-dihydro-3H-pyrazol-3-one derivatives as specific HIF-pyrolyl-4-hydroxylase inhibitors for treating cardiovascular and haematological diseases, 

Source

Source(1):

• BindingDB Database