1-Benzyl-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

ID: ALA1086473

Chembl Id: CHEMBL1086473

Cas Number: 1229024-57-0

PubChem CID: 46830489

Max Phase: Preclinical

Molecular Formula: C21H22N4

Molecular Weight: 330.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1nc2c(N)nc3ccccc3c2n1Cc1ccccc1

Standard InChI:  InChI=1S/C21H22N4/c1-2-3-13-18-24-19-20(25(18)14-15-9-5-4-6-10-15)16-11-7-8-12-17(16)23-21(19)22/h4-12H,2-3,13-14H2,1H3,(H2,22,23)

Standard InChI Key:  CQBDMXYZNLJUFT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1086473

   1-Benzyl-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

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: 330.44

Molecular Weight (Monoisotopic): 330.1844

AlogP: 4.56

#Rotatable Bonds: 5

Polar Surface Area: 56.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.87

CX LogP: 4.84

CX LogD: 4.84

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.92

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. Kokatla HP, Sil D, Malladi SS, Balakrishna R, Hermanson AR, Fox LM, Wang X, Dixit A, David SA..  (2013)  Exquisite selectivity for human toll-like receptor 8 in substituted furo[2,3-c]quinolines.,  56  (17): [PMID:23899291] [10.1021/jm400694d]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

4. Saroa R, Kaushik D, Bagai U, Kaur S, Salunke DB..  (2019)  Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host.,  29  (9): [PMID:30850167] [10.1016/j.bmcl.2019.02.029]

5. Kimani FW, Manna S, Moser B, Shen J, Nihesh N, Esser-Kahn AP..  (2021)  Improving the Adjuvanticity of Small Molecule Immune Potentiators Using Covalently Linked NF-κB Modulators.,  12  (9.0): [PMID:34527180] [10.1021/acsmedchemlett.1c00267]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data