1-(3-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(3-tert-butyl-1H-pyrazol-5-yl)urea

ID: ALA2089214

PubChem CID: 70693380

Max Phase: Preclinical

Molecular Formula: C19H22N10O

Molecular Weight: 406.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(NC(=O)Nc2cccc(Nc3ncc4c(N)n[nH]c4n3)c2)n[nH]1

Standard InChI:  InChI=1S/C19H22N10O/c1-19(2,3)13-8-14(27-26-13)24-18(30)23-11-6-4-5-10(7-11)22-17-21-9-12-15(20)28-29-16(12)25-17/h4-9H,1-3H3,(H3,23,24,26,27,30)(H4,20,21,22,25,28,29)

Standard InChI Key:  AORPMCLTISKSFU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   26.8277   -5.6583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8266   -6.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5414   -6.8985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5396   -5.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2550   -5.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2598   -6.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0473   -6.7319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5292   -6.0604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0395   -5.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2898   -4.6086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1118   -6.8976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1111   -7.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3962   -8.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3952   -8.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1099   -9.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8271   -8.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8245   -8.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5427   -9.3653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2560   -8.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9716   -9.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2537   -8.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6849   -8.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4383   -9.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9887   -8.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5742   -7.9506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7678   -8.1244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8094   -8.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1470   -9.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2925   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6333   -8.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 22 23  1  0
  5  6  1  0
  2 11  1  0
 11 12  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
  2  3  1  0
 24 27  1  0
 12 13  2  0
 27 28  1  0
  3  6  2  0
 27 29  1  0
 13 14  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089214

   1-[3-[(3-amino-2H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-(5-tert-butyl-1H-pyrazol-3-yl)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: 406.45

Molecular Weight (Monoisotopic): 406.1978

AlogP: 3.34

#Rotatable Bonds: 4

Polar Surface Area: 162.32

Molecular Species: NEUTRAL

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.46

CX Basic pKa: 3.43

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -1.51

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