3-(3-chloro-4-methoxybenzyl)-5-(3,5-dichloro-4-(3-(dimethylamino)propoxy)phenyl)pyrazin-2(1H)-one

ID: ALA2417877

PubChem CID: 72163725

Max Phase: Preclinical

Molecular Formula: C23H24Cl3N3O3

Molecular Weight: 496.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2nc(-c3cc(Cl)c(OCCCN(C)C)c(Cl)c3)c[nH]c2=O)cc1Cl

Standard InChI:  InChI=1S/C23H24Cl3N3O3/c1-29(2)7-4-8-32-22-17(25)11-15(12-18(22)26)20-13-27-23(30)19(28-20)10-14-5-6-21(31-3)16(24)9-14/h5-6,9,11-13H,4,7-8,10H2,1-3H3,(H,27,30)

Standard InChI Key:  PSMJZABXJVIVAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   17.4417   -7.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4417   -8.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1469   -8.5516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8522   -8.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8522   -7.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1469   -6.9172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5575   -6.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2643   -7.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9727   -6.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9755   -6.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2641   -5.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5585   -6.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7328   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7304   -6.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4402   -5.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4382   -4.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7288   -4.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0199   -4.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0254   -5.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7346   -8.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7253   -3.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2636   -4.8863    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.6790   -7.3430    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.6839   -5.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3910   -6.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0993   -5.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8064   -6.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5147   -5.7110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2218   -6.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5160   -4.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0158   -3.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1449   -4.4684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
  1 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  2 20  2  0
 17 21  1  0
 11 22  1  0
  9 23  1  0
 10 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 21 31  1  0
 16 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417877

   3-[(3-chloro-4-methoxyphenyl)methyl]-5-[3,5-dichloro-4-[3-(dimethylamino)propoxy]phenyl]-1H-pyrazin-2-one

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: 496.82

Molecular Weight (Monoisotopic): 495.0883

AlogP: 5.33

#Rotatable Bonds: 9

Polar Surface Area: 67.45

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.82

CX Basic pKa: 9.24

CX LogP: 4.25

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -0.75

References

1. Saha S, Reddy ChV, Xu S, Sankar S, Neamati N, Patro B..  (2013)  Synthesis and SAR studies of marine natural products ma'edamines A, B and their analogues.,  23  (18): [PMID:23927972] [10.1016/j.bmcl.2013.07.017]

Source

Source(1):

• Scientific Literature