3-(4-amino-7-(piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenol

ID: ALA450519

PubChem CID: 18792927

Max Phase: Preclinical

Molecular Formula: C17H19N5O

Molecular Weight: 309.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cccc(O)c1)cn2C1CCNCC1

Standard InChI:  InChI=1S/C17H19N5O/c18-16-15-14(11-2-1-3-13(23)8-11)9-22(17(15)21-10-20-16)12-4-6-19-7-5-12/h1-3,8-10,12,19,23H,4-7H2,(H2,18,20,21)

Standard InChI Key:  CIGMIXWAESLRNR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -4.0303  -13.5322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315  -14.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166  -14.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184  -13.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6032  -13.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983  -14.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065  -14.6117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219  -13.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143  -13.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3209  -12.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470  -15.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641  -12.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7589  -12.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086  -11.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644  -10.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738  -11.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205  -11.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975  -11.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997  -16.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432  -16.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359  -16.9594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4854  -16.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422  -15.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 11  1  0
  9 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 14 18  1  0
 11 19  1  0
  8  9  2  0
  9  5  1  0
  4  1  1  0
  4 10  1  0
  5  6  1  0
 11 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA450519

   3-(4-amino-7-(piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenol

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: 309.37

Molecular Weight (Monoisotopic): 309.1590

AlogP: 2.31

#Rotatable Bonds: 2

Polar Surface Area: 88.99

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: 10.28

CX LogP: 0.75

CX LogD: -1.09

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.04

References

1. Bamborough P, Drewry D, Harper G, Smith GK, Schneider K..  (2008)  Assessment of chemical coverage of kinome space and its implications for kinase drug discovery.,  51  (24): [PMID:19035792] [10.1021/jm8011036]

Source

Source(1):

• Scientific Literature