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

ID: ALA3408317

PubChem CID: 118730736

Max Phase: Preclinical

Molecular Formula: C20H18N4O3

Molecular Weight: 362.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ncc(C(=O)c2ccc3c(c2)n(Cc2ccccc2)c(=O)n3C)c1O

Standard InChI:  InChI=1S/C20H18N4O3/c1-22-16-9-8-14(18(25)15-11-21-23(2)19(15)26)10-17(16)24(20(22)27)12-13-6-4-3-5-7-13/h3-11,26H,12H2,1-2H3

Standard InChI Key:  VAGWCJOJLMALTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.8841    5.2815    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
   -3.6267    2.9927    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
   -5.0926    6.2452    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
   -3.6187    1.4919    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
   -4.6549    0.8867    0.0000 O   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
   -1.0028    1.5132    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
    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
    2.5889    0.0182    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
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    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
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200    4.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    4.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873    3.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1174    2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488    1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  1  6  1  0
  5  7  1  0
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 17 19  2  0
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 21 22  1  0
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 22 27  2  0
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 24 25  1  0
 25 26  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3408317

   ---

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: 362.39

Molecular Weight (Monoisotopic): 362.1379

AlogP: 2.06

#Rotatable Bonds: 4

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: 3.28

CX LogD: 1.72

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: -1.42

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