2-[3-(4-Amino-5-phenyl-pyrrolo[2,3-d]pyrimidin-7-yl)-benzylamino]-ethanol

ID: ALA176702

PubChem CID: 10451087

Max Phase: Preclinical

Molecular Formula: C21H21N5O

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccccc1)cn2-c1cccc(CNCCO)c1

Standard InChI:  InChI=1S/C21H21N5O/c22-20-19-18(16-6-2-1-3-7-16)13-26(21(19)25-14-24-20)17-8-4-5-15(11-17)12-23-9-10-27/h1-8,11,13-14,23,27H,9-10,12H2,(H2,22,24,25)

Standard InChI Key:  MDPXBTVEVMPBMF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.3426  -24.0549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3413  -24.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535  -25.2941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0515  -23.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689  -24.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695  -24.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5597  -25.1379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0475  -24.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5588  -23.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8104  -23.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6178  -22.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721  -22.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3199  -21.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103  -21.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599  -22.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137  -25.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609  -26.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155  -27.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225  -27.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8744  -26.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6169  -26.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0477  -22.8185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6811  -27.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391  -27.8168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459  -27.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0038  -28.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8107  -28.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  9 10  1  0
  5  4  2  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
 21 16  1  0
  7 16  1  0
  5  6  1  0
  4 22  1  0
 10 11  2  0
 20 23  1  0
 23 24  1  0
 11 12  1  0
 24 25  1  0
  2  3  1  0
 25 26  1  0
 12 13  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA176702

   2-(3-(4-amino-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)benzylamino)ethanol

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: 359.43

Molecular Weight (Monoisotopic): 359.1746

AlogP: 2.75

#Rotatable Bonds: 6

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: ┄

CX Basic pKa: 9.02

CX LogP: 2.68

CX LogD: 1.05

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: -0.91

References

1. Missbach M, Altmann E, Widler L, Susa M, Buchdunger E, Mett H, Meyer T, Green J..  (2000)  Substituted 5,7-diphenyl-pyrrolo[2,3d]pyrimidines: potent inhibitors of the tyrosine kinase c-Src.,  10  (9): [PMID:10853665] [10.1016/s0960-894x(00)00131-1]

2. Tintori C, Magnani M, Schenone S, Botta M..  (2009)  Docking, 3D-QSAR studies and in silico ADME prediction on c-Src tyrosine kinase inhibitors.,  44  (3): [PMID:18722033] [10.1016/j.ejmech.2008.07.002]

3. Shahlaei M, Pourhossein A.  (2013)  A 2D image-based method for modeling some c-Src tyrosine kinase inhibitors,  22  (6): [10.1007/s00044-012-0308-3]

Source

Source(1):

• Scientific Literature