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

ID: ALA2417884

PubChem CID: 72163844

Max Phase: Preclinical

Molecular Formula: C23H27N3O3

Molecular Weight: 393.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2nc(-c3ccc(OCCCN(C)C)cc3)c[nH]c2=O)cc1

Standard InChI:  InChI=1S/C23H27N3O3/c1-26(2)13-4-14-29-20-11-7-18(8-12-20)22-16-24-23(27)21(25-22)15-17-5-9-19(28-3)10-6-17/h5-12,16H,4,13-15H2,1-3H3,(H,24,27)

Standard InChI Key:  OWAVRAOXERJISB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   15.0066  -15.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0066  -16.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7119  -17.1858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4172  -16.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4172  -15.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7119  -15.5514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1224  -15.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8292  -15.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5376  -15.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5405  -14.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8290  -14.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1235  -14.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2977  -15.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2953  -14.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0052  -14.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0031  -13.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2937  -13.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5849  -13.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5904  -14.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2995  -17.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2488  -14.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9559  -14.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6642  -14.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3713  -14.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0797  -14.3452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7867  -14.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0810  -13.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2902  -12.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9962  -11.8768    0.0000 C   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
 10 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 17 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417884

   5-[4-[3-(dimethylamino)propoxy]phenyl]-3-[(4-methoxyphenyl)methyl]-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: 393.49

Molecular Weight (Monoisotopic): 393.2052

AlogP: 3.37

#Rotatable Bonds: 9

Polar Surface Area: 67.45

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.82

CX Basic pKa: 9.24

CX LogP: 2.44

CX LogD: 0.72

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -0.70

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