5-[3-(4-Chloro-phenyl)-isoxazol-5-yl]-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA2368960

Cas Number: 133040-30-9

PubChem CID: 5271258

Max Phase: Preclinical

Molecular Formula: C18H16ClN3O6

Molecular Weight: 405.79

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(-c2ccc(Cl)cc2)no1

Standard InChI:  InChI=1S/C18H16ClN3O6/c19-10-3-1-9(2-4-10)12-5-14(28-21-12)11-7-22(18(26)20-17(11)25)16-6-13(24)15(8-23)27-16/h1-5,7,13,15-16,23-24H,6,8H2,(H,20,25,26)/t13-,15+,16+/m0/s1

Standard InChI Key:  RDWMBXVEAYEJBQ-NUEKZKHPSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    1.2561   -4.3016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5615   -4.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -5.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -5.7227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712   -3.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260   -5.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -4.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820   -4.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340   -5.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -4.2536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261   -2.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538   -3.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -5.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -4.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -2.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088   -2.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -5.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -5.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109   -6.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -6.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -5.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8311   -6.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -2.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8311   -5.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -6.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5456   -6.7241    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -1.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558   -1.1271    0.0000 O   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 14  1  0
 11  5  1  0
  5 12  1  0
 13  9  1  0
 14  8  1  0
 15 11  1  0
 16 12  1  0
 17  3  2  0
 18 13  1  0
 19  6  2  0
 20 18  2  0
 21 18  1  0
 22 24  1  0
 16 23  1  6
 24 21  2  0
 25 20  1  0
 26 22  1  0
 15 27  1  1
 28 27  1  0
  4  6  1  0
 15 16  1  0
 10 13  2  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368960

   5-(3-(4-Chloro-phenyl)-isoxazol-5-yl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-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: 405.79

Molecular Weight (Monoisotopic): 405.0728

AlogP: 1.15

#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: 9.64

CX Basic pKa: ┄

CX LogP: 1.08

CX LogD: 1.07

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -0.28

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