2-amino-8-(beta-D-ribofuranosyl)imidazo[1,2-a]-s-triazin-4-one 5'-monophosphate

ID: ALA3275942

Cas Number: 67410-66-6

PubChem CID: 90679295

Max Phase: Preclinical

Molecular Formula: C10H14N5O8P

Molecular Weight: 363.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n2ccn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C10H14N5O8P/c11-8-12-9-14(1-2-15(9)10(18)13-8)7-6(17)5(16)4(23-7)3-22-24(19,20)21/h1-2,4-7,16-17H,3H2,(H2,11,13,18)(H2,19,20,21)/t4-,5-,6-,7-/m1/s1

Standard InChI Key:  PHYKWIBWRMBPJM-DBRKOABJSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    6.4727  -15.6340    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.4823  -16.4588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1918  -16.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6313  -10.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6302  -11.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3449  -12.2222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431  -10.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583  -10.9784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0586  -11.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8490  -12.0660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3373  -11.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8485  -10.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154  -12.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3406   -9.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041  -12.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6216  -13.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1067  -14.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8912  -13.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8909  -13.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017  -14.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8768  -14.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6105  -12.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6164  -14.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6478  -15.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  1  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  5 13  1  0
  7 14  2  0
 15 10  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 17 20  1  1
 20 21  1  0
 19 22  1  6
 18 23  1  6
 21  1  1  0
  1 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275942

   2-Amino-8-(5-O-phosphono-beta-D-ribofuranosyl)imidazo[1,2-a]-1,3,5-triazin-4(8H)-one

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: 363.22

Molecular Weight (Monoisotopic): 363.0580

AlogP: -2.80

#Rotatable Bonds: 4

Polar Surface Area: 194.66

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: 3.05

CX LogP: -2.79

CX LogD: -6.22

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.35

Np Likeness Score: 0.81

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