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

ID: ALA175409

PubChem CID: 10432113

Max Phase: Preclinical

Molecular Formula: C23H23N5O3

Molecular Weight: 417.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cn(-c3ccc(CC(=O)NCCO)cc3)c3ncnc(N)c23)c1

Standard InChI:  InChI=1S/C23H23N5O3/c1-31-18-4-2-3-16(12-18)19-13-28(23-21(19)22(24)26-14-27-23)17-7-5-15(6-8-17)11-20(30)25-9-10-29/h2-8,12-14,29H,9-11H2,1H3,(H,25,30)(H2,24,26,27)

Standard InChI Key:  FPPFXZVOJMZPIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.2360    1.2650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477    0.0245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457    1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    1.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4554    0.1809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9438    0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545    1.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064    2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5147    2.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165    3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060    3.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1552    2.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7097   -0.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2190   -2.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7716   -1.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137   -0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    2.5028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4755   -2.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5761    3.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    2.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2827   -3.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5393   -3.9058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8336   -2.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3465   -4.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030   -4.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4102   -5.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 19 23  1  0
 12 24  1  0
 11 12  1  0
 24 25  1  0
  2  3  1  0
 23 26  1  0
 12 13  2  0
 26 27  1  0
  3  6  2  0
 26 28  2  0
 13 14  1  0
 27 29  1  0
  1  2  2  0
 29 30  1  0
 14 15  2  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA175409

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

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: 417.47

Molecular Weight (Monoisotopic): 417.1801

AlogP: 2.33

#Rotatable Bonds: 7

Polar Surface Area: 115.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.79

CX LogP: 2.02

CX LogD: 2.01

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.97

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