6-((4'-Chloro-[1,1'-biphenyl]-4-yl)oxy)-3-hydroxy-1-methylpyrimidine-2,4(1H,3H)-dione

ID: ALA4534109

PubChem CID: 129907026

Max Phase: Preclinical

Molecular Formula: C17H13ClN2O4

Molecular Weight: 344.75

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(Oc2ccc(-c3ccc(Cl)cc3)cc2)cc(=O)n(O)c1=O

Standard InChI:  InChI=1S/C17H13ClN2O4/c1-19-16(10-15(21)20(23)17(19)22)24-14-8-4-12(5-9-14)11-2-6-13(18)7-3-11/h2-10,23H,1H3

Standard InChI Key:  WVQNVPZFGSIBJX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   13.3811  -24.4812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -25.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -25.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -26.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8101  -26.9562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5245  -26.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2390  -26.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9535  -26.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9535  -25.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6679  -25.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3824  -25.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0969  -25.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0969  -24.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8114  -24.0687    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.3824  -24.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6679  -24.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2390  -25.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5245  -25.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -26.9562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -27.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -26.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -25.7187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9522  -25.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9522  -26.9562    0.0000 O   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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 10 16  1  0
  9 17  1  0
 17 18  2  0
  6 18  1  0
  4 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  2 22  1  0
 22 23  1  0
 21 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534109

   ---

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: 344.75

Molecular Weight (Monoisotopic): 344.0564

AlogP: 2.90

#Rotatable Bonds: 3

Polar Surface Area: 73.46

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.44

CX Basic pKa: ┄

CX LogP: 3.56

CX LogD: 1.73

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.47

References

1. Tang J, Liu F, Nagy E, Miller L, Kirby KA, Wilson DJ, Wu B, Sarafianos SG, Parniak MA, Wang Z..  (2016)  3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations.,  59  (6): [PMID:26927866] [10.1021/acs.jmedchem.5b01879]

Source

Source(1):

• Scientific Literature