2-methoxyethoxy-8-oxo-9-(4-carboxybenzyl)adenine

ID: ALA4637769

Cas Number: 1062444-54-5

PubChem CID: 58019867

Product Number: T345642, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H17N5O5

Molecular Weight: 359.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCCOc1nc(N)c2[nH]c(=O)n(Cc3ccc(C(=O)O)cc3)c2n1

Standard InChI:  InChI=1S/C16H17N5O5/c1-25-6-7-26-15-19-12(17)11-13(20-15)21(16(24)18-11)8-9-2-4-10(5-3-9)14(22)23/h2-5H,6-8H2,1H3,(H,18,24)(H,22,23)(H2,17,19,20)

Standard InChI Key:  ATISKRYGYNSRNP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.6193   -3.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182   -4.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3329   -5.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3312   -3.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -3.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0468   -4.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8329   -5.0613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3185   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8325   -3.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3287   -2.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1435   -4.3921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0416   -5.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8375   -6.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0449   -6.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8399   -7.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4268   -6.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2132   -5.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4185   -5.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2231   -6.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4341   -7.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8082   -6.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034   -5.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1893   -4.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745   -5.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7604   -4.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -5.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
  8 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
  2 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637769

   TLR7 agonist T7

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: 359.34

Molecular Weight (Monoisotopic): 359.1230

AlogP: 0.47

#Rotatable Bonds: 7

Polar Surface Area: 145.35

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: 2.77

CX LogP: 1.24

CX LogD: -1.64

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: -0.84

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]

2. Szekely T,Roy O,Dériaud E,Job A,Lo-Man R,Leclerc C,Taillefumier C.  (2018)  Design, Synthesis, and Immunological Evaluation of a Multicomponent Construct Based on a Glycotripeptoid Core Comprising B and T Cell Epitopes and a Toll-like Receptor 7 Agonist That Elicits Potent Immune Responses.,  61  (21.0): [PMID:30351939] [10.1021/acs.jmedchem.8b00960]

Source

Source(1):

• Scientific Literature