4-Amino-6-(4-methoxybenzyl)-3-(2-(4-methoxybenzylidene)hydrazinyl)-1,2,4-triazin-5(4H)-one

ID: ALA2013090

PubChem CID: 70693720

Max Phase: Preclinical

Molecular Formula: C19H20N6O3

Molecular Weight: 380.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N/Nc2nnc(Cc3ccc(OC)cc3)c(=O)n2N)cc1

Standard InChI:  InChI=1S/C19H20N6O3/c1-27-15-7-3-13(4-8-15)11-17-18(26)25(20)19(24-22-17)23-21-12-14-5-9-16(28-2)10-6-14/h3-10,12H,11,20H2,1-2H3,(H,23,24)/b21-12+

Standard InChI Key:  TXSJENBPDJZEHV-CIAFOILYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.4346    0.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -0.9122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598    0.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472    0.7380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -0.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743   -0.9173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2900   -0.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0044   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7160   -0.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086    0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -1.7372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7072    0.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205    0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -0.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -0.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131   -0.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -0.9247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487   -0.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4307   -0.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1460   -0.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1476    0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4281    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8627    0.7261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5778    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  2  0
  3 14  1  0
  1  2  1  0
 13 15  2  0
  4  8  1  0
 15 16  1  0
  1  6  2  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  2  3  1  0
 18 19  2  0
 19 13  1  0
  9 10  2  0
 17 20  1  0
  3  4  1  0
 20 21  1  0
 10 11  1  0
 11 22  2  0
  4  5  2  0
 22 23  1  0
 23 24  2  0
  5  6  1  0
 24 25  1  0
  1 12  1  0
 25 26  2  0
 26 11  1  0
 24 27  1  0
 12 13  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2013090

   4-amino-6-[(4-methoxyphenyl)methyl]-3-[(2E)-2-[(4-methoxyphenyl)methylidene]hydrazinyl]-1,2,4-triazin-5-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: 380.41

Molecular Weight (Monoisotopic): 380.1597

AlogP: 1.41

#Rotatable Bonds: 7

Polar Surface Area: 116.65

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: 2.47

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.11

References

1. El Massry AM, Asal AM, Khattab SN, Haiba NS, Awney HA, Helmy M, Langer V, Amer A..  (2012)  Synthesis and structure elucidation of novel fused 1,2,4-triazine derivatives as potent inhibitors targeting CYP1A1 activity.,  20  (8): [PMID:22414679] [10.1016/j.bmc.2012.02.041]

Source

Source(1):

• Scientific Literature