5-(3-Methoxy-phenyl)-7-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

ID: ALA172973

PubChem CID: 15858662

Max Phase: Preclinical

Molecular Formula: C19H16N4O

Molecular Weight: 316.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cn(-c3ccccc3)c3ncnc(N)c23)c1

Standard InChI:  InChI=1S/C19H16N4O/c1-24-15-9-5-6-13(10-15)16-11-23(14-7-3-2-4-8-14)19-17(16)18(20)21-12-22-19/h2-12H,1H3,(H2,20,21,22)

Standard InChI Key:  JSPJGKUIWGWCRE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   13.6499    0.9248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6486    0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3607   -0.3142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3588    1.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0760    0.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0765    0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8667   -0.1580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3546    0.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8659    1.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1175    1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9248    2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1789    2.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6269    3.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8174    3.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5669    2.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1208   -0.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5680   -1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8225   -2.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6295   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1813   -1.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9238   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3548    2.1612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9849    3.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5365    2.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA172973

   5-(3-Methoxyphenyl)-7-phenyl-4-aminopyrrolo[2,3-d]pyrimidine

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: 316.36

Molecular Weight (Monoisotopic): 316.1324

AlogP: 3.68

#Rotatable Bonds: 3

Polar Surface Area: 65.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.79

CX LogP: 3.65

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.92

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