1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d]imidazol-2(3H)-one

ID: ALA3408339

PubChem CID: 118730758

Max Phase: Preclinical

Molecular Formula: C18H22N4O3

Molecular Weight: 342.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)n(CC)c2cc(C(=O)c3c(C)nn(C)c3O)ccc21

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

Standard InChI Key:  WAYTXTJHGKWJLS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.2917   -0.7475    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
   -3.6187    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841    5.2815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549    0.8867    0.0000 O   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
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3841    5.2767    0.0000 N   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
   -5.9808    3.4673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8430    3.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0926    6.2452    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
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160    3.8564    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
   -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
   -1.2757    3.4825    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
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330   -4.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 17  1  0
 21  1  2  0
  9 20  2  0
  8 14  1  0
 17 15  1  0
  8 12  1  0
  1  6  1  0
 13 12  2  0
 19  9  1  0
  6  7  1  0
 18 13  1  0
  3  9  1  0
 16  1  1  0
 16 19  2  0
  4 18  2  0
 13  3  1  0
  6 11  1  0
  8  4  1  0
 20 21  1  0
  7  2  2  0
 17 16  1  0
  3  5  2  0
 12 10  1  0
 18 22  1  0
 15 23  1  0
 11 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3408339

   ---

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: 2.21

#Rotatable Bonds: 5

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: 3.76

CX Basic pKa: 2.54

CX LogP: 2.75

CX LogD: 1.36

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -1.39

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