2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-{[({[(phosphonatooxy)phosphinato]oxy}(sulfanidyl)phosphoryl)oxy]methyl}oxolan-2-yl]-7-methyl-6-oxido-9H-purin-7-ium

ID: ALA4298680

PubChem CID: 145994349

Max Phase: Preclinical

Molecular Formula: C11H20N5O13P3S

Molecular Weight: 555.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1cn([C@@H]2O[C@H](CO[P@@](=O)(S)OP(=O)(O)OP(=O)([O-])O)[C@@H](O)[C@H]2O)c2c1C(O)NC(N)=N2

Standard InChI:  InChI=1S/C11H20N5O13P3S/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(27-10)2-26-32(25,33)29-31(23,24)28-30(20,21)22/h3-4,6-7,9-10,17-19H,2H2,1H3,(H6-,12,13,14,20,21,22,23,24,25,33)/t4-,6-,7-,9?,10-,32-/m1/s1

Standard InChI Key:  GDVFMBGQRVGNSJ-KOCQAOCKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    7.2927  -24.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1211  -24.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0498  -23.3313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0593  -21.9969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5697  -22.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8396  -22.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8339  -23.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5462  -23.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2648  -23.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2665  -22.2595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5536  -21.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5557  -21.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9776  -23.5052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8093  -21.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3853  -23.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6120  -24.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3935  -24.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5953  -23.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0662  -25.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3657  -25.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8608  -23.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195  -23.2173    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4353  -23.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6940  -23.3161    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098  -23.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685  -23.4150    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5842  -23.8759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150  -24.0424    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6858  -24.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2608  -24.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0932  -22.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6858  -22.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2608  -22.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 15  1  0
 15 18  1  0
 18  2  1  0
  2 16  1  0
  9 10  1  0
 17 19  1  6
 16 20  1  6
 15  3  1  1
  2  1  1  1
 10 11  1  0
  1 21  1  0
 11  6  1  0
 21 22  1  0
  3  7  1  0
 22 23  1  0
 11 12  1  0
 23 24  1  0
  6  7  2  0
 24 25  1  0
  9 13  1  0
 25 26  1  0
  6  4  1  0
 26 27  1  0
  4 14  1  0
 22 28  1  6
  7  8  1  0
 24 29  1  0
 16 17  1  0
 26 30  1  0
  4  5  2  0
 22 31  2  0
  8  9  2  0
 24 32  2  0
  5  3  1  0
 26 33  2  0
M  CHG  2   4   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4298680

   ---

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: 555.29

Molecular Weight (Monoisotopic): 554.9991

AlogP: -2.88

#Rotatable Bonds: 8

Polar Surface Area: 271.56

Molecular Species: ACID

HBA: 15

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.68

CX Basic pKa: 6.59

CX LogP: -6.75

CX LogD: -13.02

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.09

Np Likeness Score: 1.02

References

1. Kowalska J, Lukaszewicz M, Zuberek J, Ziemniak M, Darzynkiewicz E, Jemielity J..  (2009)  Phosphorothioate analogs of m7GTP are enzymatically stable inhibitors of cap-dependent translation.,  19  (7): [PMID:19269171] [10.1016/j.bmcl.2009.02.053]

Source

Source(1):

• Scientific Literature