(2-methyl-4-(methylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)(phenyl)methanone

ID: ALA454084

PubChem CID: 12023163

Max Phase: Preclinical

Molecular Formula: C14H13N5O

Molecular Weight: 267.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C)nc2c(C(=O)c3ccccc3)cnn12

Standard InChI:  InChI=1S/C14H13N5O/c1-9-17-13-11(8-16-19(13)14(15-2)18-9)12(20)10-6-4-3-5-7-10/h3-8H,1-2H3,(H,15,17,18)

Standard InChI Key:  VBOCKEFYRKUQPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.6471  -11.9349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471  -12.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327  -13.1724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327  -11.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2182  -11.9349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2182  -12.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336  -13.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513  -12.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336  -11.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327  -10.6974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471  -10.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616  -13.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786  -13.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307  -14.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283  -13.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833  -14.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902  -14.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2423  -14.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9873  -13.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804  -13.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0
  4 10  1  0
  5  6  1  0
 10 11  1  0
  2 12  1  0
  2  3  2  0
  3  6  1  0
  1  2  1  0
 13 14  2  0
 13 15  1  0
  7 13  1  0
  5  4  1  0
 15 16  2  0
  6  7  2  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA454084

   [2-Methyl-4-(methylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl]-phenylmethanone

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: 267.29

Molecular Weight (Monoisotopic): 267.1120

AlogP: 1.71

#Rotatable Bonds: 3

Polar Surface Area: 72.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.49

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: -1.43

References

1. Raboisson P, Schultz D, Muller C, Reimund JM, Pinna G, Mathieu R, Bernard P, Do QT, Desjarlais RL, Justiano H, Lugnier C, Bourguignon JJ..  (2008)  Cyclic nucleotide phosphodiesterase type 4 inhibitors: evaluation of pyrazolo[1,5-a]-1,3,5-triazine ring system as an adenine bioisostere.,  43  (4): [PMID:17640774] [10.1016/j.ejmech.2007.05.016]

Source

Source(1):

• Scientific Literature