8-(beta-D-ribofuranosyl)imidazo[1,2-a]-s-triazine-2,4-dione

ID: ALA3275943

PubChem CID: 90679296

Max Phase: Preclinical

Molecular Formula: C10H12N4O6

Molecular Weight: 284.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1nc2n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)ccn2c(=O)[nH]1

Standard InChI:  InChI=1S/C10H12N4O6/c15-3-4-5(16)6(17)7(20-4)13-1-2-14-9(13)11-8(18)12-10(14)19/h1-2,4-7,15-17H,3H2,(H,12,18,19)/t4-,5-,6-,7-/m1/s1

Standard InChI Key:  DVPHWFHIQKXSOW-DBRKOABJSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   13.6278  -10.8549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6265  -11.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3412  -12.0948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3394  -10.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0545  -10.8513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0548  -11.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8450  -11.9387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3331  -11.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8446  -10.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3368   -9.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1001  -12.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6177  -13.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1026  -14.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8870  -13.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8867  -12.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6977  -14.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8731  -14.7870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6062  -12.5756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6120  -14.1966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9120  -12.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  6  2  0
  5  4  1  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  2  0
 11  7  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 13 16  1  1
 16 17  1  0
 15 18  1  6
 14 19  1  6
  2 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275943

   8-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazo[1,2-a][1,3,5]triazine-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: 284.23

Molecular Weight (Monoisotopic): 284.0757

AlogP: -3.20

#Rotatable Bonds: 2

Polar Surface Area: 142.08

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.02

CX Basic pKa: 2.18

CX LogP: -2.25

CX LogD: -3.54

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 0.76

References

1. Kim SH, Bartholomew DG, Allen LB, Robins RK, Revankar GR..  (1978)  Imidazo[1,2-a]-s-triazine nucleosides. Synthesis and antiviral activity of the N-bridgehead guanine, guanosine, and guanosine monophosphate analogues of imidazo[1,2-a]-s-triazine.,  21  (9): [PMID:214563] [10.1021/jm00207a009]

Source

Source(1):

• Scientific Literature