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

ID: ALA4760461

PubChem CID: 162658015

Max Phase: Preclinical

Molecular Formula: C19H26ClN5O4

Molecular Weight: 423.90

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H26ClN5O4/c1-18(2,29)13(8-3-4-8)22-15-10-16(24-17(20)23-15)25(7-21-10)11-9-5-19(9,6-26)14(28)12(11)27/h7-9,11-14,26-29H,3-6H2,1-2H3,(H,22,23,24)/t9-,11-,12+,13+,14+,19+/m1/s1

Standard InChI Key:  MCIHPCYNMCALBM-LXKAJCFWSA-N

Molfile:  

 
     RDKit          2D

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   27.5575  -27.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3788  -27.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6332  -26.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0722  -28.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8584  -28.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4142  -26.7172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4845  -25.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6634  -25.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7380  -26.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0756  -27.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1607  -28.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9074  -28.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5699  -27.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4816  -27.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1413  -26.5648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8888  -26.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3032  -26.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9577  -26.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2108  -26.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9496  -25.6672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.5092  -26.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3025  -25.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9940  -29.1541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.5485  -26.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9766  -27.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3168  -28.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7241  -28.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1870  -28.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3580  -26.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8758  -25.6627    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
 16 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 29 24  1  0
 30 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760461

   ---

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: 423.90

Molecular Weight (Monoisotopic): 423.1673

AlogP: 0.72

#Rotatable Bonds: 6

Polar Surface Area: 136.55

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.21

CX Basic pKa: 1.71

CX LogP: -0.13

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 0.67

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