1-(2,4-dichloro-5-hydroxybenzyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one

ID: ALA4072166

PubChem CID: 137639597

Max Phase: Preclinical

Molecular Formula: C15H12Cl2N2O2

Molecular Weight: 323.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)n(Cc2cc(O)c(Cl)cc2Cl)c2ccccc21

Standard InChI:  InChI=1S/C15H12Cl2N2O2/c1-18-12-4-2-3-5-13(12)19(15(18)21)8-9-6-14(20)11(17)7-10(9)16/h2-7,20H,8H2,1H3

Standard InChI Key:  KGRKNWWLCTXQOC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    5.3775   -6.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0872   -5.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0843   -5.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3757   -4.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -5.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.8633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4113   -5.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939   -6.1844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6446   -6.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -5.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6330   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773   -3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752   -3.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5194   -3.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2639   -2.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592   -2.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9186   -2.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8074   -1.6513    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.3193   -3.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178   -2.5435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
  8 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 15 20  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072166

   ---

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: 323.18

Molecular Weight (Monoisotopic): 322.0276

AlogP: 3.40

#Rotatable Bonds: 2

Polar Surface Area: 47.16

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.35

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -1.07

References

1. Fujimoto J, Okamoto R, Noguchi N, Hara R, Masada S, Kawamoto T, Nagase H, Tamura YO, Imanishi M, Takagahara S, Kubo K, Tohyama K, Iida K, Andou T, Miyahisa I, Matsui J, Hayashi R, Maekawa T, Matsunaga N..  (2017)  Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors.,  60  (21): [PMID:29023121] [10.1021/acs.jmedchem.7b01210]

Source

Source(1):

• Scientific Literature