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: ALA3351004

PubChem CID: 145948197

Max Phase: Preclinical

Molecular Formula: C11H18N5O13P3S

Molecular Weight: 553.28

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)c2nc(N)nc(O)c21

Standard InChI:  InChI=1S/C11H18N5O13P3S/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/h3-4,6-7,10,17-18H,2H2,1H3,(H6-,12,13,14,19,20,21,22,23,24,25,33)/t4-,6-,7-,10-,32+/m1/s1

Standard InChI Key:  OTIKKVINVWNBOQ-FGPCVGTKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   10.9865  -16.4334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2452  -16.0710    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5609  -16.5319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8196  -16.1699    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.1354  -16.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3941  -16.2687    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7099  -16.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2407  -16.8961    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115  -16.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865  -17.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2188  -15.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115  -15.3461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865  -15.4461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4087  -17.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2336  -17.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1623  -16.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1718  -14.8719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6822  -15.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9521  -15.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9464  -15.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6587  -16.3742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3773  -15.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3790  -15.1345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6661  -14.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6682  -13.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0901  -16.3802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9218  -14.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4978  -16.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7245  -17.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5060  -17.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7078  -16.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1787  -18.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4782  -18.5786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 18 16  1  0
  4  5  1  0
  6 10  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
  2 11  2  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  4 12  2  0
 23 24  2  0
 24 19  1  0
  1  2  1  0
 24 25  1  0
  6 13  2  0
 22 26  1  0
  6  7  1  0
 17 27  1  0
  3  4  1  0
 29 30  1  0
  2  8  1  1
 16 20  1  0
 30 28  1  0
 28 31  1  0
 31 15  1  0
 15 29  1  0
  4  9  1  0
 30 32  1  6
 19 17  1  0
 29 33  1  6
 28 16  1  1
 15 14  1  1
 14  1  1  0
M  CHG  2   9  -1  17   1
M  END

Alternative Forms

1. Parent:

   

   ALA3351004

   ---

2. Alternative Forms:

   

   ALA3351004

   ---

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: 553.28

Molecular Weight (Monoisotopic): 552.9835

AlogP: -2.19

#Rotatable Bonds: 8

Polar Surface Area: 272.95

Molecular Species: ACID

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.66

CX Basic pKa: 2.12

CX LogP: -7.28

CX LogD: -11.22

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.10

Np Likeness Score: 0.94

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