4-Methyl-1-pentyl-1H-benzo[d]imidazol-2-amine

ID: ALA3326930

Chembl Id: CHEMBL3326930

Cas Number: 1622856-77-2

PubChem CID: 90647157

Max Phase: Preclinical

Molecular Formula: C13H19N3

Molecular Weight: 217.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCn1c(N)nc2c(C)cccc21

Standard InChI:  InChI=1S/C13H19N3/c1-3-4-5-9-16-11-8-6-7-10(2)12(11)15-13(16)14/h6-8H,3-5,9H2,1-2H3,(H2,14,15)

Standard InChI Key:  BWGFTWWXYOBSIL-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3326930

   4-Methyl-1-pentyl-1H-benzimidazol-2-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: 217.32

Molecular Weight (Monoisotopic): 217.1579

AlogP: 3.12

#Rotatable Bonds: 4

Polar Surface Area: 43.84

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.98

CX LogP: 3.62

CX LogD: 3.00

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.80

Np Likeness Score: -0.98

References

1. Beesu M, Malladi SS, Fox LM, Jones CD, Dixit A, David SA..  (2014)  Human Toll-like receptor 8-selective agonistic activities in 1-alkyl-1H-benzimidazol-2-amines.,  57  (17): [PMID:25102141] [10.1021/jm500701q]

2. Beesu M, Salyer AC, Trautman KL, Hill JK, David SA..  (2016)  Human Toll-like Receptor (TLR) 8-Specific Agonistic Activity in Substituted Pyrimidine-2,4-diamines.,  59  (17): [PMID:27513008] [10.1021/acs.jmedchem.6b00872]

3. Beesu M,Caruso G,Salyer AC,Shukla NM,Khetani KK,Smith LJ,Fox LM,Tanji H,Ohto U,Shimizu T,David SA.  (2016)  Identification of a Human Toll-Like Receptor (TLR) 8-Specific Agonist and a Functional Pan-TLR Inhibitor in 2-Aminoimidazoles.,  59  (7.0): [PMID:26966993] [10.1021/acs.jmedchem.6b00023]

4. Talukdar A, Ganguly D, Roy S, Das N, Sarkar D..  (2021)  Structural Evolution and Translational Potential for Agonists and Antagonists of Endosomal Toll-like Receptors.,  64  (12.0): [PMID:34107682] [10.1021/acs.jmedchem.1c00300]

Source

Source(1):

• Scientific Literature