(1R,2R,3S,4R,5S)-4-(6-((R)-1-cyclopropyl-2-methylpropylamino)-2-iodo-9H-purin-9-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol

ID: ALA4743059

PubChem CID: 162647063

Max Phase: Preclinical

Molecular Formula: C19H26IN5O3

Molecular Weight: 499.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H](Nc1nc(I)nc2c1ncn2[C@H]1[C@H](O)[C@H](O)[C@]2(CO)C[C@H]12)C1CC1

Standard InChI:  InChI=1S/C19H26IN5O3/c1-8(2)11(9-3-4-9)22-16-12-17(24-18(20)23-16)25(7-21-12)13-10-5-19(10,6-26)15(28)14(13)27/h7-11,13-15,26-28H,3-6H2,1-2H3,(H,22,23,24)/t10-,11-,13-,14+,15+,19+/m1/s1

Standard InChI Key:  QRTOZRNSWLTZJK-XRPRFISDSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   39.6585  -19.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4798  -19.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7342  -18.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1732  -20.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9594  -20.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5152  -18.6650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.5855  -17.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.7644  -17.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8390  -18.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1767  -19.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2617  -19.9565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0085  -20.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6710  -19.8046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.5826  -18.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2423  -18.5126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.9898  -18.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4042  -18.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0588  -18.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3118  -18.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0506  -17.6150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.6102  -18.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4036  -17.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.0951  -21.1019    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   45.6496  -18.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4591  -18.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9768  -17.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0776  -19.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4179  -20.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8251  -19.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 18  1  0
 17  1  1  0
  1  4  1  6
  2  5  1  6
  3  6  1  1
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  1  0
 18 17  1  0
 19 18  1  0
 17 19  1  0
 18 20  1  1
 17 21  1  1
 21 22  1  0
 12 23  1  0
 16 24  1  1
 25 24  1  0
 26 25  1  0
 24 26  1  0
 16 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743059

   ---

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: 499.35

Molecular Weight (Monoisotopic): 499.1080

AlogP: 1.55

#Rotatable Bonds: 6

Polar Surface Area: 116.32

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: 1.80

CX LogP: 1.25

CX LogD: 1.25

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: 0.69

References

1. Tosh DK,Toti KS,Hurst BL,Julander JG,Jacobson KA.  (2020)  Structure activity relationship of novel antiviral nucleosides against Enterovirus A71.,  30  (23): [PMID:33031923] [10.1016/j.bmcl.2020.127599]

Source

Source(1):

• Scientific Literature