N-(3-(3,4-dichlorobenzyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-2-hydroxyacetamide

ID: ALA444433

PubChem CID: 25158453

Max Phase: Preclinical

Molecular Formula: C17H13Cl2N3O3

Molecular Weight: 378.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CO)Nc1ccc2ncn(Cc3ccc(Cl)c(Cl)c3)c(=O)c2c1

Standard InChI:  InChI=1S/C17H13Cl2N3O3/c18-13-3-1-10(5-14(13)19)7-22-9-20-15-4-2-11(21-16(24)8-23)6-12(15)17(22)25/h1-6,9,23H,7-8H2,(H,21,24)

Standard InChI Key:  ZZCPRLFJMWBCSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.7167  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7167  -13.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046  -13.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046  -11.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2961  -13.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5874  -13.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294  -13.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1329  -12.2102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804  -11.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780  -10.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496  -11.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619  -12.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554  -13.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2668  -13.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845  -13.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862  -12.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741  -11.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4323  -11.7938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456  -12.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8613  -11.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432  -13.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5745  -12.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7013  -11.8096    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6973  -13.4654    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
  1  2  1  0
 12 13  1  0
  1  4  2  0
 13 14  2  0
  2  3  2  0
 14 15  1  0
  3  6  1  0
 15 16  2  0
  5  4  1  0
 16 17  1  0
  5 10  1  0
 17 18  2  0
 18 13  1  0
  6  7  1  0
  1 19  1  0
  7  8  2  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 20 22  2  0
  5  6  2  0
 21 23  1  0
 10 11  2  0
 17 24  1  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA444433

   N-(3-(3,4-dichlorobenzyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-2-hydroxyacetamide

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: 378.21

Molecular Weight (Monoisotopic): 377.0334

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 84.22

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: 4.65

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.73

References

1. Koltun DO, Vasilevich NI, Parkhill EQ, Glushkov AI, Zilbershtein TM, Mayboroda EI, Boze MA, Cole AG, Henderson I, Zautke NA, Brunn SA, Chu N, Hao J, Mollova N, Leung K, Chisholm JW, Zablocki J..  (2009)  Orally bioavailable, liver-selective stearoyl-CoA desaturase (SCD) inhibitors.,  19  (11): [PMID:19394219] [10.1016/j.bmcl.2009.04.004]

2. Koltun DO, Zilbershtein TM, Migulin VA, Vasilevich NI, Parkhill EQ, Glushkov AI, McGregor MJ, Brunn SA, Chu N, Hao J, Mollova N, Leung K, Chisholm JW, Zablocki J..  (2009)  Potent, orally bioavailable, liver-selective stearoyl-CoA desaturase (SCD) inhibitors.,  19  (15): [PMID:19577469] [10.1016/j.bmcl.2009.06.017]

3. Deng Y, Yang Z, Shipps GW, Lo SM, West R, Hwa J, Zheng S, Farley C, Lachowicz J, van Heek M, Bass AS, Sinha DP, Mahon CR, Cartwright ME..  (2013)  Discovery of liver-targeted inhibitors of stearoyl-CoA desaturase (SCD1).,  23  (3): [PMID:23265904] [10.1016/j.bmcl.2012.11.075]

Source

Source(1):

• Scientific Literature