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

ID: ALA4647035

PubChem CID: 156021107

Max Phase: Preclinical

Molecular Formula: C22H28N6O9

Molecular Weight: 520.50

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](O)[C@@H]4O)cc3)c2n1

Standard InChI:  InChI=1S/C22H28N6O9/c1-35-6-7-36-21-25-17(23)13-18(26-21)28(22(34)24-13)8-10-2-4-11(5-3-10)19(33)27-20-16(32)15(31)14(30)12(9-29)37-20/h2-5,12,14-16,20,29-32H,6-9H2,1H3,(H,24,34)(H,27,33)(H2,23,25,26)/t12-,14-,15+,16+,20?/m1/s1

Standard InChI Key:  QKAXNCJSCUTXKM-YMOCPUBESA-N

Molfile:  

 
     RDKit          2D

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   20.8248  -25.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.1646  -27.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  2  0
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 35 30  1  0
 33 36  1  0
 36 10  1  0
 36 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4647035

   ---

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: 520.50

Molecular Weight (Monoisotopic): 520.1918

AlogP: -2.28

#Rotatable Bonds: 9

Polar Surface Area: 227.56

Molecular Species: NEUTRAL

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.45

CX Basic pKa: 3.37

CX LogP: -1.07

CX LogD: -1.07

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.15

Np Likeness Score: -0.14

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