1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

ID: ALA1085742

Cas Number: 1020412-43-4

PubChem CID: 44592366

Product Number: G274801, Order Now?

Max Phase: Preclinical

Molecular Formula: C17H23N5O

Molecular Weight: 313.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): Gardiquimod

Canonical SMILES:  CCNCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O

Standard InChI:  InChI=1S/C17H23N5O/c1-4-19-9-13-21-14-15(22(13)10-17(2,3)23)11-7-5-6-8-12(11)20-16(14)18/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20)

Standard InChI Key:  FHJATBIERQTCTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.6556    1.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9437    1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6568    0.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3696    0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3688   -0.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6493   -1.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394   -0.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284    1.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4360    0.3306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9541    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439    1.6678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    2.6420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1291    1.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    1.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041    1.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124    2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1765   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -1.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  9  2  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
  5  6  2  0
  2 14  1  0
  2  1  1  0
 12 15  1  0
  6  7  1  0
 15 16  1  0
  1  4  2  0
 16 17  1  0
  7  8  2  0
 17 18  1  0
  8  3  1  0
 11 19  1  0
  9 10  1  0
 19 20  1  0
  3 10  2  0
 20 21  1  0
  3  4  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1085742

   Gardiquimod diTFA

2. Parent:

   

   ALA1085742

   Gardiquimod

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 313.40

Molecular Weight (Monoisotopic): 313.1903

AlogP: 2.05

#Rotatable Bonds: 5

Polar Surface Area: 88.99

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.34

CX LogP: 1.40

CX LogD: 0.41

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.67

Np Likeness Score: -0.58

References

1. Shukla NM, Malladi SS, Mutz CA, Balakrishna R, David SA..  (2010)  Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues.,  53  (11): [PMID:20481492] [10.1021/jm100358c]

2. Patinote C, Karroum NB, Moarbess G, Cirnat N, Kassab I, Bonnet PA, Deleuze-Masquéfa C..  (2020)  Agonist and antagonist ligands of toll-like receptors 7 and 8: Ingenious tools for therapeutic purposes.,  193  [PMID:32203790] [10.1016/j.ejmech.2020.112238]

3. Zhang J, Zhang Y, Qu B, Yang H, Hu S, Dong X..  (2021)  If small molecules immunotherapy comes, can the prime be far behind?,  218  [PMID:33773287] [10.1016/j.ejmech.2021.113356]

Source

Source(1):

• Scientific Literature