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

ID: ALA2368957

Cas Number: 133040-39-8

PubChem CID: 5271263

Max Phase: Preclinical

Molecular Formula: C13H15N3O5

Molecular Weight: 293.28

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-n1cccc1

Standard InChI:  InChI=1S/C13H15N3O5/c17-7-10-9(18)5-11(21-10)16-6-8(12(19)14-13(16)20)15-3-1-2-4-15/h1-4,6,9-11,17-18H,5,7H2,(H,14,19,20)/t9-,10+,11+/m0/s1

Standard InChI Key:  ULODFGLWHBNVRA-HBNTYKKESA-N

Molfile:  

     RDKit          2D

 21 23  0  0  1  0  0  0  0  0999 V2000
    2.8708   -3.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1762   -4.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -4.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0202   -5.4030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913   -3.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9967   -4.4768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6409   -2.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5609   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -2.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -2.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148   -4.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -5.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5488   -5.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4092   -3.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2162   -3.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3024   -4.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5214   -2.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -1.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -0.8074    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  5  1  0
  5 10  1  0
 11  9  1  0
 12 10  1  0
 13  3  2  0
 14  6  2  0
 15  8  1  0
 16  8  1  0
 17 16  2  0
 18 15  2  0
 12 19  1  6
 11 20  1  1
 21 20  1  0
  4  6  1  0
 11 12  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2368957

   1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-pyrrol-1-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: 293.28

Molecular Weight (Monoisotopic): 293.1012

AlogP: -1.03

#Rotatable Bonds: 3

Polar Surface Area: 109.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: -0.50

CX LogD: -0.50

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 0.32

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