2-[4-(4-Chlorobenzyloxy)-3-cyano]phenylpyrimidine-4-ol

ID: ALA4866811

PubChem CID: 164621794

Max Phase: Preclinical

Molecular Formula: C18H12ClN3O2

Molecular Weight: 337.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2nccc(O)n2)ccc1OCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C18H12ClN3O2/c19-15-4-1-12(2-5-15)11-24-16-6-3-13(9-14(16)10-20)18-21-8-7-17(23)22-18/h1-9H,11H2,(H,21,22,23)

Standard InChI Key:  GQRQVKBGOCGKHI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   17.5063  -12.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5051  -13.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2132  -13.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9228  -13.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9200  -12.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2114  -11.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6232  -11.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3327  -12.3881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0384  -11.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0357  -11.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3215  -10.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6188  -11.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7971  -13.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2159  -14.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2157  -15.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3156   -9.9365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0897  -13.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3817  -13.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6751  -13.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9675  -13.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9664  -14.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6788  -14.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3834  -14.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2589  -14.8435    0.0000 Cl  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
 17 18  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
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866811

   ---

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: 337.77

Molecular Weight (Monoisotopic): 337.0618

AlogP: 3.95

#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: 4.69

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -1.50

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