N-[(2S,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-N-{2-[(2R,5S)-2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-ethyl}-4-nitro-benzenesulfonamide

ID: ALA4794435

PubChem CID: 162674174

Max Phase: Preclinical

Molecular Formula: C28H32N12O11S

Molecular Weight: 744.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CN(CCO[C@@H]2[C@H](O)[C@@H](CO)O[C@H]2n2cnc3c(N)ncnc32)S(=O)(=O)c2ccc([N+](=O)[O-])cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C28H32N12O11S/c29-23-17-25(33-9-31-23)38(11-35-17)27-21(44)19(42)15(50-27)7-37(52(47,48)14-3-1-13(2-4-14)40(45)46)5-6-49-22-20(43)16(8-41)51-28(22)39-12-36-18-24(30)32-10-34-26(18)39/h1-4,9-12,15-16,19-22,27-28,41-44H,5-8H2,(H2,29,31,33)(H2,30,32,34)/t15-,16-,19-,20-,21-,22-,27-,28-/m1/s1

Standard InChI Key:  AMGWTFVKYNMMDE-DWVGVLABSA-N

Molfile:  

 
     RDKit          2D

 52 58  0  0  0  0  0  0  0  0999 V2000
   12.0845   -9.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7944   -9.8063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7933   -8.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0592   -9.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8764   -9.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1308   -8.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4678   -8.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8091   -8.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0318   -8.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8615   -7.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5780  -10.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3560  -10.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1688   -9.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6484  -10.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4612  -10.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9407  -11.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6075  -11.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8119  -12.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7256  -12.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4718  -13.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0192  -12.6752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2040  -11.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0174  -13.3565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6408  -14.0815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9083   -8.3737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5711   -8.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2329   -8.3722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0986  -14.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5065  -15.3962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1642   -7.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9791   -7.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3879   -6.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9829   -6.1876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1649   -6.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7598   -6.8913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2050   -6.8971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3922  -14.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3040  -15.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9595  -15.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7034  -15.3734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7879  -14.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1316  -14.0859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8718  -16.5146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6072   -9.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0810  -10.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8931  -10.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2304   -9.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7496   -8.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9391   -8.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0469   -9.4835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3826   -8.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5243  -10.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  8  9  1  1
  9 10  1  0
  4 11  1  6
  5 12  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 18 22  1  6
 19 23  1  6
 20 24  1  1
  6 25  1  1
 25 26  1  0
 26 27  2  0
 27 31  1  0
 30 25  1  0
 24 28  1  0
 28 29  2  0
 29 38  1  0
 37 24  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 32 36  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 37  1  0
 39 43  1  0
 15  2  1  0
  2 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 44  1  0
 50 51  2  0
 50 52  1  0
 47 50  1  0
M  CHG  2  50   1  52  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4794435

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 744.70

Molecular Weight (Monoisotopic): 744.2034

AlogP: -2.32

#Rotatable Bonds: 12

Polar Surface Area: 328.37

Molecular Species: NEUTRAL

HBA: 21

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.35

CX Basic pKa: 5.22

CX LogP: -2.23

CX LogD: -2.23

Aromatic Rings: 5

Heavy Atoms: 52

QED Weighted: 0.06

Np Likeness Score: -0.01

References

1. Ahmed-Belkacem R,Sutto-Ortiz P,Guiraud M,Canard B,Vasseur JJ,Decroly E,Debart F.  (2020)  Synthesis of adenine dinucleosides SAM analogs as specific inhibitors of SARS-CoV nsp14 RNA cap guanine-N7-methyltransferase.,  201  [PMID:32563813] [10.1016/j.ejmech.2020.112557]

Source

Source(1):

• Scientific Literature