5-fluoro-2-(1-(2-fluoro-3-methylbenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidin-4-ol

ID: ALA3810301

PubChem CID: 71621106

Max Phase: Preclinical

Molecular Formula: C18H13F2N5O2

Molecular Weight: 369.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(Cn2nc(-c3ncc(F)c(O)n3)cc2-c2ccon2)c1F

Standard InChI:  InChI=1S/C18H13F2N5O2/c1-10-3-2-4-11(16(10)20)9-25-15(13-5-6-27-24-13)7-14(23-25)17-21-8-12(19)18(26)22-17/h2-8H,9H2,1H3,(H,21,22,26)

Standard InChI Key:  VQPILUYEENTSEO-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 C   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:

   

   ALA3810301

   5-fluoro-2-[1-[(2-fluoro-3-methylphenyl)methyl]-5-(1,2-oxazol-3-yl)pyrazol-3-yl]-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: 369.33

Molecular Weight (Monoisotopic): 369.1037

AlogP: 3.34

#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: 4.38

CX LogD: 4.38

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -1.64

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