1-(4-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(3-chloro-4-fluorophenyl)urea

ID: ALA2089215

PubChem CID: 70687101

Max Phase: Preclinical

Molecular Formula: C18H14ClFN8O

Molecular Weight: 412.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n[nH]c2nc(Nc3ccc(NC(=O)Nc4ccc(F)c(Cl)c4)cc3)ncc12

Standard InChI:  InChI=1S/C18H14ClFN8O/c19-13-7-11(5-6-14(13)20)25-18(29)24-10-3-1-9(2-4-10)23-17-22-8-12-15(21)27-28-16(12)26-17/h1-8H,(H2,24,25,29)(H4,21,22,23,26,27,28)

Standard InChI Key:  CMZDJOPDAAAGNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.5307  -12.5654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5319  -13.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832  -13.8059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814  -12.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968  -12.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9017  -13.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894  -13.6393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714  -12.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815  -12.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9319  -11.5155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2469  -13.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475  -14.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626  -15.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9636  -15.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2487  -16.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314  -15.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5339  -15.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483  -17.1043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9627  -17.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775  -17.1050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623  -18.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920  -17.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1070  -17.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209  -17.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209  -18.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1011  -18.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3901  -18.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337  -17.1065    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5345  -18.7590    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 15 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 19 21  2  0
  9 10  1  0
 20 22  1  0
  5  6  1  0
 22 23  2  0
  2 11  1  0
 23 24  1  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 27 22  1  0
 12 13  2  0
 24 28  1  0
  3  6  2  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089215

   1-[4-[(3-amino-2H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-(3-chloro-4-fluorophenyl)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: 412.82

Molecular Weight (Monoisotopic): 412.0963

AlogP: 4.12

#Rotatable Bonds: 4

Polar Surface Area: 133.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.63

CX Basic pKa: 3.43

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.85

References

1. Yang LL, Li GB, Yan HX, Sun QZ, Ma S, Ji P, Wang ZR, Feng S, Zou J, Yang SY..  (2012)  Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization.,  56  [PMID:22944772] [10.1016/j.ejmech.2012.08.007]

Source

Source(1):

• Scientific Literature