(E)-3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)acrylonitrile

ID: ALA4069201

PubChem CID: 56840684

Max Phase: Preclinical

Molecular Formula: C19H19N5O

Molecular Weight: 333.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2c(/C=C/C#N)n(CCCO)c3ncnc(N)c23)cc1

Standard InChI:  InChI=1S/C19H19N5O/c1-13-5-7-14(8-6-13)16-15(4-2-9-20)24(10-3-11-25)19-17(16)18(21)22-12-23-19/h2,4-8,12,25H,3,10-11H2,1H3,(H2,21,22,23)/b4-2+

Standard InChI Key:  LPADWFDQODOOMS-DUXPYHPUSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.5064   -5.7082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5053   -6.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2201   -6.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2182   -5.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9337   -5.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9385   -6.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7304   -6.7877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2150   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7224   -5.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9899   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4415   -8.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7009   -8.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1525   -9.5865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2158   -4.4704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9728   -4.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7780   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0284   -3.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4725   -3.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6630   -3.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4164   -4.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7218   -2.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0399   -6.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4566   -6.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2816   -6.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1099   -6.8126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  4 14  1  0
  9 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069201

   (E)-3-(4-Amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)acrylonitrile

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: 333.40

Molecular Weight (Monoisotopic): 333.1590

AlogP: 2.91

#Rotatable Bonds: 5

Polar Surface Area: 100.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.05

CX LogP: 2.34

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.46

References

1. Jackson PA, Widen JC, Harki DA, Brummond KM..  (2017)  Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.,  60  (3): [PMID:27996267] [10.1021/acs.jmedchem.6b00788]

Source

Source(1):

• Scientific Literature