4-[[6-amino-8-hydroxy-2-(2-methoxyethoxy)purin-9-yl]methyl]-N-[(3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]benzamide

ID: ALA4645661

PubChem CID: 156019597

Max Phase: Preclinical

Molecular Formula: C28H38N6O14

Molecular Weight: 682.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCOc1nc(N)c2nc(O)n(Cc3ccc(C(=O)NC4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)cc3)c2n1

Standard InChI:  InChI=1S/C28H38N6O14/c1-44-6-7-45-27-31-22(29)15-23(32-27)34(28(43)30-15)8-11-2-4-12(5-3-11)24(42)33-25-19(40)18(39)21(14(10-36)46-25)48-26-20(41)17(38)16(37)13(9-35)47-26/h2-5,13-14,16-21,25-26,35-41H,6-10H2,1H3,(H,30,43)(H,33,42)(H2,29,31,32)/t13-,14-,16-,17+,18-,19-,20-,21-,25?,26-/m1/s1

Standard InChI Key:  JBAXVFHKCUHXIC-YWVGKLDKSA-N

Molfile:  

 
     RDKit          2D

 49 53  0  0  0  0  0  0  0  0999 V2000
    9.5215   -7.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5215   -8.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2346   -9.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9476   -8.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9476   -7.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2346   -7.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8047   -7.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2346  -10.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6625   -9.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6643   -7.5643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8023   -6.7388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8065   -9.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0939   -8.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0971   -7.9873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3884   -7.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6761   -7.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6768   -8.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3900   -9.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0861   -9.6241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3944  -10.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649   -7.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9653   -9.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889   -6.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6778   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6196   -3.1653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6185   -3.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3344   -4.4043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3326   -2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0489   -3.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492   -3.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8361   -4.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3237   -3.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8356   -2.9031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3300   -1.9246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1492   -3.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068   -4.4033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -3.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4758   -4.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606   -3.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0447   -4.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8280   -5.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5396   -5.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267   -6.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2374   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9579   -6.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9632   -5.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2520   -5.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6698   -6.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3847   -6.3324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  1
  3  8  1  1
  4  9  1  6
  5 10  1  0
  7 11  1  0
  2 12  1  6
 12 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  1
 18 20  1  6
 16 21  1  6
 17 22  1  1
 15 23  1  1
 23 24  1  0
 25 26  2  0
 26 27  1  0
 27 30  2  0
 29 28  2  0
 28 25  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
 28 34  1  0
 32 35  1  0
 26 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 31 41  1  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 42  1  0
 45 48  1  0
 48 10  1  0
 48 49  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4645661

   ---

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: 682.64

Molecular Weight (Monoisotopic): 682.2446

AlogP: -4.46

#Rotatable Bonds: 12

Polar Surface Area: 306.71

Molecular Species: NEUTRAL

HBA: 19

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.39

CX Basic pKa: 3.37

CX LogP: -2.84

CX LogD: -2.84

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.08

Np Likeness Score: 0.39

References

1. Baba A, Wakao M, Shinchi H, Chan M, Hayashi T, Yao S, Cottam HB, Carson DA, Suda Y..  (2020)  Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands.,  30  (3): [PMID:31864800] [10.1016/j.bmcl.2019.126840]

Source

Source(1):

• Scientific Literature