2-((2-(1-(2-aminoethyl)piperidin-4-ylamino)-4-methyl-1H-benzo[d]imidazol-1-yl)methyl)-6-methylpyridin-3-ol

ID: ALA242456

Cas Number: 317846-22-3

PubChem CID: 511013

Max Phase: Preclinical

Molecular Formula: C22H30N6O

Molecular Weight: 394.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: JNJ-240806 | JNJ-2408068 | R-170591 | JNJ-2408068|317846-22-3|JNJ 2408068|R-170591|AB821DL88A|2-[[2-[[1-(2-aminoethyl)piperidin-4-yl]amino]-4-methylbenzimidazol-1-yl]methyl]-6-methylpyridin-3-ol|JNJ-240806|2-[[2-[[1-(2-Azanylethyl)piperidin-4-Yl]amino]-4-Methyl-Benzimidazol-1-Yl]methyl]-6-Methyl-Pyridin-3-Ol|R 170591|UNII-AB821DL88A|3-PYRIDINOL, 2-((2-((1-(2-AMINOETHYL)-4-PIPERIDINYL)AMINO)-4-METHYL-1H-BENZIMIDAZOL-1-YL)METHYL)-6-METHYL-|3-Pyridinol, 2-[[2-[[1-(2-aminoethyl)-4-piperidinyl]amino]Show More⌵

Canonical SMILES:  Cc1ccc(O)c(Cn2c(NC3CCN(CCN)CC3)nc3c(C)cccc32)n1

Standard InChI:  InChI=1S/C22H30N6O/c1-15-4-3-5-19-21(15)26-22(25-17-8-11-27(12-9-17)13-10-23)28(19)14-18-20(29)7-6-16(2)24-18/h3-7,17,29H,8-14,23H2,1-2H3,(H,25,26)

Standard InChI Key:  RDQSNNMSDOHAPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.7291   -1.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -1.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129   -0.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    0.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4419   -1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -0.0381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7172   -0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309   -1.3803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -2.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5422   -0.7075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9536    0.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5387    0.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7718    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876    0.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1805    2.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7641    2.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1728    3.5894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    0.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153    1.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919    1.3802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    2.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082    2.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6233    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4483    2.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  6  7  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
 15 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  1  0
  4  6  1  0
  7 21  1  0
  1 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
  8 11  1  0
 23 24  1  0
  1  2  2  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
  5  1  1  0
 24 28  1  0
  2  3  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA242456

   JNJ 2408068

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: 394.52

Molecular Weight (Monoisotopic): 394.2481

AlogP: 2.64

#Rotatable Bonds: 6

Polar Surface Area: 92.23

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.00

CX Basic pKa: 9.22

CX LogP: 1.35

CX LogD: -0.22

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.02

References

1. Bonfanti JF, Doublet F, Fortin J, Lacrampe J, Guillemont J, Muller P, Queguiner L, Arnoult E, Gevers T, Janssens P, Szel H, Willebrords R, Timmerman P, Wuyts K, Janssens F, Sommen C, Wigerinck P, Andries K..  (2007)  Selection of a respiratory syncytial virus fusion inhibitor clinical candidate, part 1: improving the pharmacokinetic profile using the structure-property relationship.,  50  (19): [PMID:17722899] [10.1021/jm070143x]

2. Bonfanti JF, Meyer C, Doublet F, Fortin J, Muller P, Queguiner L, Gevers T, Janssens P, Szel H, Willebrords R, Timmerman P, Wuyts K, van Remoortere P, Janssens F, Wigerinck P, Andries K..  (2008)  Selection of a respiratory syncytial virus fusion inhibitor clinical candidate. 2. Discovery of a morpholinopropylaminobenzimidazole derivative (TMC353121).,  51  (4): [PMID:18254606] [10.1021/jm701284j]

3. Narasimhan B, Sharma D, Kumar P.  (2012)  Benzimidazole: a medicinally important heterocyclic moiety,  21  (3): [10.1007/s00044-010-9533-9]

4. Zheng X, Liang C, Wang L, Wang B, Liu Y, Feng S, Wu JZ, Gao L, Feng L, Chen L, Guo T, Shen HC, Yun H..  (2018)  Discovery of Benzoazepinequinoline (BAQ) Derivatives as Novel, Potent, Orally Bioavailable Respiratory Syncytial Virus Fusion Inhibitors.,  61  (22): [PMID:30339388] [10.1021/acs.jmedchem.8b01394]

Source

Source(1):

• Scientific Literature