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

ID: ALA2089212

PubChem CID: 70682868

Max Phase: Preclinical

Molecular Formula: C18H14ClFN8O

Molecular Weight: 412.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n[nH]c2nc(Nc3cccc(NC(=O)Nc4ccc(F)c(Cl)c4)c3)ncc12

Standard InChI:  InChI=1S/C18H14ClFN8O/c19-13-7-11(4-5-14(13)20)25-18(29)24-10-3-1-2-9(6-10)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:  GAOZHXLWEXPTEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   10.4444   -6.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4432   -7.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1581   -7.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1563   -5.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8716   -6.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8765   -7.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6640   -7.2694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1459   -6.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6561   -5.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9065   -5.1461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7284   -7.4351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7278   -8.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0129   -8.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0119   -9.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7266   -9.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4437   -9.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4412   -8.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1593   -9.9028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8727   -9.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5883   -9.8989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8704   -8.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3016   -9.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0150   -9.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7279   -9.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7261   -8.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0054   -8.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2955   -8.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0003   -7.4238    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4389   -8.2437    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
 16 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
 26 28  1  0
  3  6  2  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089212

   1-[3-[(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: 11.40

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: -1.96

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