{3-[4-Amino-5-(3-methoxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-phenyl}-methanol

ID: ALA176815

PubChem CID: 44385116

Max Phase: Preclinical

Molecular Formula: C20H18N4O2

Molecular Weight: 346.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cn(-c3cccc(CO)c3)c3ncnc(N)c23)c1

Standard InChI:  InChI=1S/C20H18N4O2/c1-26-16-7-3-5-14(9-16)17-10-24(15-6-2-4-13(8-15)11-25)20-18(17)19(21)22-12-23-20/h2-10,12,25H,11H2,1H3,(H2,21,22,23)

Standard InChI Key:  DHKJMXHLKKNTKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   13.7295  -15.9836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7281  -16.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4404  -17.2228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4384  -15.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1559  -15.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1564  -16.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9466  -17.0665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4345  -16.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9457  -15.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1974  -14.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0048  -14.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2591  -13.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7069  -13.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8973  -13.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6468  -14.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2007  -17.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6478  -18.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9024  -19.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7094  -19.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2614  -18.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0039  -18.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4346  -14.7471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0652  -13.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6167  -14.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0681  -18.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3262  -19.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  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
 12 23  1  0
 23 24  1  0
 11 12  1  0
 20 25  1  0
  2  3  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA176815

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

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: 346.39

Molecular Weight (Monoisotopic): 346.1430

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 86.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.79

CX LogP: 2.89

CX LogD: 2.87

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -0.70

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