1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-2-methylphenyl)-3-(5-tert-butylisoxazol-3-yl)urea

ID: ALA4475159

PubChem CID: 118489455

Max Phase: Preclinical

Molecular Formula: C20H21N7O3

Molecular Weight: 407.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(Oc2ncnc3[nH]ncc23)ccc1NC(=O)Nc1cc(C(C)(C)C)on1

Standard InChI:  InChI=1S/C20H21N7O3/c1-11-7-12(29-18-13-9-23-26-17(13)21-10-22-18)5-6-14(11)24-19(28)25-16-8-15(30-27-16)20(2,3)4/h5-10H,1-4H3,(H,21,22,23,26)(H2,24,25,27,28)

Standard InChI Key:  UGIGANGJJUVAIR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   14.6147  -17.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8203  -18.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4048  -18.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1671  -17.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1730  -16.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8925  -15.8888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6020  -16.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3591  -15.9773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9078  -16.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4915  -17.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6808  -17.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4594  -15.8755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7440  -16.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303  -15.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3108  -16.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7339  -17.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0144  -17.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3049  -17.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5853  -17.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5795  -18.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2890  -18.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2830  -19.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0672  -19.8378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5592  -19.1753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0794  -18.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5635  -19.9829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8540  -19.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8599  -18.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3313  -18.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0357  -15.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  7 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 21 25  1  0
 22 26  2  0
 26 27  1  0
 27 28  2  0
 20 28  1  0
 10  2  1  0
  2 29  1  0
 14 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475159

   1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-methyl-4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]urea

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 407.43

Molecular Weight (Monoisotopic): 407.1706

AlogP: 4.38

#Rotatable Bonds: 4

Polar Surface Area: 130.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.03

CX Basic pKa: 1.19

CX LogP: 3.92

CX LogD: 3.82

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -2.10

References

1. Li GB, Ma S, Yang LL, Ji S, Fang Z, Zhang G, Wang LJ, Zhong JM, Xiong Y, Wang JH, Huang SZ, Li LL, Xiang R, Niu D, Chen YC, Yang SY..  (2016)  Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model.,  59  (18): [PMID:27535613] [10.1021/acs.jmedchem.6b00604]

Source

Source(1):

• Scientific Literature