3'-((1-Hydroxy-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)oxy)-[1,1'-biphenyl]-4-carbonitrile

ID: ALA4476701

PubChem CID: 129907024

Max Phase: Preclinical

Molecular Formula: C18H13N3O4

Molecular Weight: 335.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(Oc2cccc(-c3ccc(C#N)cc3)c2)cc(=O)n(O)c1=O

Standard InChI:  InChI=1S/C18H13N3O4/c1-20-17(10-16(22)21(24)18(20)23)25-15-4-2-3-14(9-15)13-7-5-12(11-19)6-8-13/h2-10,24H,1H3

Standard InChI Key:  RFHPPBLTFNJLSQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.3042  -18.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3118  -19.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0300  -19.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0376  -20.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7558  -20.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4665  -20.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1847  -20.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8954  -20.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6136  -20.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6212  -21.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3394  -22.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0501  -21.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7683  -22.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4865  -22.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0425  -20.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3242  -20.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8878  -19.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1695  -19.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4589  -19.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3269  -21.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3345  -21.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6087  -20.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6011  -19.7734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8829  -19.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8981  -21.0174    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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  3  0
 12 15  1  0
 15 16  2  0
  9 16  1  0
  8 17  2  0
 17 18  1  0
 18 19  2  0
  6 19  1  0
  4 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  2 23  1  0
 23 24  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476701

   ---

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: 335.32

Molecular Weight (Monoisotopic): 335.0906

AlogP: 2.12

#Rotatable Bonds: 3

Polar Surface Area: 97.25

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.44

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 0.98

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.74

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