2-(1-(3-chloro-2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)-5-fluoropyrimidin-4-ol

ID: ALA3808807

PubChem CID: 71620794

Max Phase: Preclinical

Molecular Formula: C17H10ClF2N5O2

Molecular Weight: 389.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1nc(-c2cc(-c3ccon3)n(Cc3cccc(Cl)c3F)n2)ncc1F

Standard InChI:  InChI=1S/C17H10ClF2N5O2/c18-10-3-1-2-9(15(10)20)8-25-14(12-4-5-27-24-12)6-13(23-25)16-21-7-11(19)17(26)22-16/h1-7H,8H2,(H,21,22,26)

Standard InChI Key:  CZQLBQGCAVFYDE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.2524   -0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0317    0.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2526   -1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -2.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6461   -3.9967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4977   -5.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9352   -4.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9720   -3.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    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 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
    6.1035    2.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5736    2.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0739    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0995    5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247    4.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1243    3.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451    5.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4998    6.3836    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  5  6  1  0
  4 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
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  2 18  1  0
 22 24  1  0
 21 25  1  0
 17 26  1  0
 16 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808807

   2-[1-[(3-chloro-2-fluorophenyl)methyl]-5-(1,2-oxazol-3-yl)pyrazol-3-yl]-5-fluoro-1H-pyrimidin-6-one

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: 389.75

Molecular Weight (Monoisotopic): 389.0491

AlogP: 3.68

#Rotatable Bonds: 4

Polar Surface Area: 89.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.79

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.80

References

1. Nakai T, Perl NR, Barden TC, Carvalho A, Fretzen A, Germano P, Im GY, Jin H, Kim C, Lee TW, Long K, Moore J, Rohde JM, Sarno R, Segal C, Solberg EO, Tobin J, Zimmer DP, Currie MG..  (2016)  Discovery of IWP-051, a Novel Orally Bioavailable sGC Stimulator with Once-Daily Dosing Potential in Humans.,  7  (5): [PMID:27190594] [10.1021/acsmedchemlett.5b00479]

Source

Source(1):

• Scientific Literature