1-(4-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)phenyl)-3-(3,4-dichlorophenyl)urea

ID: ALA565255

PubChem CID: 45483779

Max Phase: Preclinical

Molecular Formula: C19H14Cl2N6O

Molecular Weight: 413.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ccn2-c1ccc(NC(=O)Nc2ccc(Cl)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C19H14Cl2N6O/c20-15-6-3-12(9-16(15)21)26-19(28)25-11-1-4-13(5-2-11)27-8-7-14-17(22)23-10-24-18(14)27/h1-10H,(H2,22,23,24)(H2,25,26,28)

Standard InChI Key:  QGDYELVPVSSWKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -4.8803    1.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815    1.0392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1666    0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4503    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1684    2.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4497    1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    2.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774    3.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0001    3.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0116    2.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    1.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7860    1.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    2.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711    3.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939    3.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    2.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    1.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4449    0.9538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490    0.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276   -0.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310   -1.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569   -1.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775   -0.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6716    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    2.2788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0620   -1.9198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -1.9006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  3  4  2  0
 14 15  2  0
 15 10  1  0
  4  6  1  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 17 19  1  0
  9  5  1  0
 19 20  1  0
  5  1  1  0
 20 21  2  0
  7 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 10 11  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 12  1  0
  1 26  1  0
  2  3  1  0
 23 27  1  0
 12 13  2  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA565255

   1-[4-(4-Aminopyrrolo[2,3-d]pyrimidin-7-yl)phenyl]-3-(3,4-dichlorophenyl)urea

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: 413.27

Molecular Weight (Monoisotopic): 412.0606

AlogP: 4.95

#Rotatable Bonds: 3

Polar Surface Area: 97.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: 5.92

CX LogP: 4.52

CX LogD: 4.50

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.44

References

1. Jung MH, Kim H, Choi WK, El-Gamal MI, Park JH, Yoo KH, Sim TB, Lee SH, Baek D, Hah JM, Cho JH, Oh CH..  (2009)  Synthesis of pyrrolo[2,3-d]pyrimidine derivatives and their antiproliferative activity against melanoma cell line.,  19  (23): [PMID:19857963] [10.1016/j.bmcl.2009.10.051]

Source

Source(1):

• Scientific Literature