1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(3-phenyl-isoxazol-5-yl)-1H-pyrimidine-2,4-dione

ID: ALA2368958

Cas Number: 133070-83-4

PubChem CID: 5271257

Max Phase: Preclinical

Molecular Formula: C18H17N3O6

Molecular Weight: 371.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1-c1cc(-c2ccccc2)no1

Standard InChI:  InChI=1S/C18H17N3O6/c22-9-15-13(23)7-16(26-15)21-8-11(17(24)19-18(21)25)14-6-12(20-27-14)10-4-2-1-3-5-10/h1-6,8,13,15-16,22-23H,7,9H2,(H,19,24,25)/t13-,15+,16+/m0/s1

Standard InChI Key:  OMVJZCCMNRCBRW-NUEKZKHPSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    1.6840   -3.7547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894   -4.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -4.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -5.1758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1990   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538   -5.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044   -3.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -4.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3619   -4.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293   -3.7067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540   -2.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -3.5351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156   -4.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865   -1.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191   -2.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -4.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387   -5.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8300   -4.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655   -2.0477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865   -0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0721   -0.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8300   -5.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445   -4.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2590   -4.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5445   -6.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2590   -5.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  8  2  0
 10 13  1  0
 11  5  1  0
  5 12  1  0
 13  8  1  0
 14  9  1  0
 15 11  1  0
 16 12  1  0
 17  3  2  0
 18  6  2  0
 19 14  1  0
 16 20  1  6
 15 21  1  1
 22 21  1  0
 23 19  2  0
 24 19  1  0
 25 24  2  0
 26 23  1  0
 27 25  1  0
  4  6  1  0
 15 16  1  0
 10 14  2  0
 27 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368958

   1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(3-phenyl-isoxazol-5-yl)-1H-pyrimidine-2,4-dione

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: 371.35

Molecular Weight (Monoisotopic): 371.1117

AlogP: 0.50

#Rotatable Bonds: 4

Polar Surface Area: 130.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.49

CX Basic pKa: ┄

CX LogP: 0.47

CX LogD: 0.47

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.10

References

1. Wigerinck P, Snoeck R, Claes P, De Clercq E, Herdewijn P..  (1991)  Synthesis and antiviral activity of 5-heteroaryl-substituted 2'-deoxyuridines.,  34  (6): [PMID:2061920] [10.1021/jm00110a003]

Source

Source(1):

• Scientific Literature