General Information of the Compound
Compound ID
CP0233638
Compound Name
1-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
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Synonyms
1-(4-Amino-2-ethoxymethyl-imidazo[4,5-c]quinolin-1-yl)-2-methyl-propan-2-ol
1-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
4-amino-2-(ethoxymethyl)-a,a-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol
4-amino-2-ethoxymethyl-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol
R 848
R-848
Resiquimod
Resiquimod [INN]
S 28463
S-28463
VML-600
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Structure
Formula
C17H22N4O2
Molecular Weight
314.389
Canonical SMILES
CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O
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InChI
InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)
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InChIKey
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
CAS
171742-32-8
208711-44-8
144875-48-9
Physicochemical Property
logP
2.4741
Rotatable Bonds
5
Heavy Atom Count
23
Polar Areas
86.19
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Complexity
23

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 159603
SID: 12014952
ChEMBL ID
CHEMBL383322
DrugBank ID
DB06530
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT02160, Toll-like receptor 7
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000752 PBMC iPSC #1 Homo sapiens (Human)  1
1
Activity = 4.478514 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  6
1
EC50 = 75 nM
   TI
   LI
   LO
   TS
2
EC50 = 260.1 nM
   TI
   LI
   LO
   TS
3
EC50 = 750 nM
   TI
   LI
   LO
   TS
4
EC50 = 1340 nM
   TI
   LI
   LO
   TS
5
EC50 = 1400 nM
   TI
   LI
   LO
   TS
6
EC50 = 1500 nM
   TI
   LI
   LO
   TS
CL000870 HEK-Blue Null1-v Homo sapiens (Human)  1
1
EC50 = 250 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Activity = 39.759534 nM
Protein ID: PT02546, Toll-like receptor 8
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000752 PBMC iPSC #1 Homo sapiens (Human)  1
1
Activity = 62.820064 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  6
1
EC50 = 480 nM
   TI
   LI
   LO
   TS
2
EC50 = 4000 nM
   TI
   LI
   LO
   TS
3
EC50 = 4500 nM
   TI
   LI
   LO
   TS
4
EC50 = 5870 nM
   TI
   LI
   LO
   TS
5
EC50 = 6130 nM
   TI
   LI
   LO
   TS
6
EC50 = 6400 nM
   TI
   LI
   LO
   TS
CL000870 HEK-Blue Null1-v Homo sapiens (Human)  1
1
EC50 = 3000 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Resiquimod )
Drug Name Resiquimod
Company 3M Pharma.
Indication
Actinic keratosis
Phase 2
Cutaneous T-cell lymphoma
Phase 2
Herpes simplex virus infection
Phase 1/2
Target(s)
Toll-like receptor 7 (TLR7)
Modulator
Toll-like receptor 8 (TLR8)
Modulator