1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3408322

PubChem CID: 118730741

Max Phase: Preclinical

Molecular Formula: C18H22N4O3

Molecular Weight: 342.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c(=O)n(C(C)(C)C)c2cc(C(=O)c3cnn(C)c3O)ccc21

Standard InChI:  InChI=1S/C18H22N4O3/c1-6-21-13-8-7-11(15(23)12-10-19-20(5)16(12)24)9-14(13)22(17(21)25)18(2,3)4/h7-10,24H,6H2,1-5H3

Standard InChI Key:  RTIMRSCEOBTDJY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5020    1.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2729   -1.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5274   -2.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2652   -0.2078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0380    0.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -2.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153   -0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4598   -0.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217   -1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -3.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574   -2.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585   -3.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  2  1  0
 19 16  1  0
  1 17  1  0
  7  5  1  0
  4  8  2  0
 12  3  1  0
 14 16  1  0
 13 15  1  0
  3 14  2  0
 10 19  1  0
  8 10  1  0
 10  5  2  0
  7 11  1  0
 15 18  2  0
  7  4  1  0
 19  9  2  0
  3 20  1  0
 17 20  2  0
 20 13  1  0
  5  6  1  0
 15 12  1  0
 16  1  2  0
 12 21  1  0
  2 22  1  0
 21 23  1  0
 21 24  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3408322

   ---

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: 342.40

Molecular Weight (Monoisotopic): 342.1692

AlogP: 2.25

#Rotatable Bonds: 3

Polar Surface Area: 82.05

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.63

CX Basic pKa: 1.55

CX LogP: 2.97

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.29

References

1. Xu YL, Lin HY, Ruan X, Yang SG, Hao GF, Yang WC, Yang GF..  (2015)  Synthesis and bioevaluation of pyrazole-benzimidazolone hybrids as novel human 4-Hydroxyphenylpyruvate dioxygenase inhibitors.,  92  [PMID:25590863] [10.1016/j.ejmech.2015.01.018]

Source

Source(1):

• Scientific Literature