2-[3-Cyano-4-(4-tert-butylbenzyloxy)]phenylpyrimidine-4-ol

ID: ALA4857117

PubChem CID: 164610317

Max Phase: Preclinical

Molecular Formula: C22H21N3O2

Molecular Weight: 359.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(COc2ccc(-c3nccc(O)n3)cc2C#N)cc1

Standard InChI:  InChI=1S/C22H21N3O2/c1-22(2,3)18-7-4-15(5-8-18)14-27-19-9-6-16(12-17(19)13-23)21-24-11-10-20(26)25-21/h4-12H,14H2,1-3H3,(H,24,25,26)

Standard InChI Key:  QMBFRCJBEHLILL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.9963  -22.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7043  -23.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4140  -22.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4112  -22.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7025  -21.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1143  -21.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8238  -22.1655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5295  -21.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5269  -20.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8127  -20.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1099  -20.9440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2883  -23.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7071  -24.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7069  -25.0348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8067  -19.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5809  -22.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8728  -23.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1662  -22.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587  -23.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4576  -24.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1699  -24.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8746  -24.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7501  -24.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0422  -24.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7505  -25.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0379  -25.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
  2 13  1  0
 14 15  3  0
  3 14  1  0
 11 16  1  0
 13 17  1  0
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 18 19  2  0
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 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4857117

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.43

Molecular Weight (Monoisotopic): 359.1634

AlogP: 4.60

#Rotatable Bonds: 4

Polar Surface Area: 79.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.55

CX Basic pKa: 0.94

CX LogP: 5.72

CX LogD: 5.72

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -1.36

References

1. Sun M, Zhao J, Mao Q, Yan C, Zhang B, Yang Y, Dai X, Gao J, Lin F, Duan Y, Zhang T, Wang S..  (2021)  Synthesis and biological evaluation of 2-(4-alkoxy-3-cyano)phenylpyrimidine derivatives with 4-amino or 4-hydroxy as a pharmacophore element binding with xanthine oxidase active site.,  38  [PMID:33838610] [10.1016/j.bmc.2021.116117]

Source

Source(1):

• Scientific Literature