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

ID: ALA176309

PubChem CID: 44385080

Max Phase: Preclinical

Molecular Formula: C18H13ClN4

Molecular Weight: 320.78

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13ClN4/c19-13-6-4-5-12(9-13)15-10-23(14-7-2-1-3-8-14)18-16(15)17(20)21-11-22-18/h1-11H,(H2,20,21,22)

Standard InChI Key:  KKYWVNPRFIJNKB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -4.7122   -8.0983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7136   -8.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0014   -9.3373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0034   -7.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861   -8.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856   -8.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -9.1811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076   -8.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -7.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447   -7.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -6.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -6.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352   -5.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447   -5.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -6.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414   -9.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941  -10.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5397  -11.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327  -11.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808  -10.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383  -10.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0073   -6.8620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772   -5.9310    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA176309

   5-(3-Chlorophenyl)-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: 320.78

Molecular Weight (Monoisotopic): 320.0829

AlogP: 4.32

#Rotatable Bonds: 2

Polar Surface Area: 56.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.80

CX LogP: 4.41

CX LogD: 4.40

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.21

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