1-(1-(3-aminophenyl)-3-tert-butyl-1H-pyrazol-5-yl)-3-(4-chlorophenyl)urea

ID: ALA498947

PubChem CID: 25210518

Max Phase: Preclinical

Molecular Formula: C20H22ClN5O

Molecular Weight: 383.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(NC(=O)Nc2ccc(Cl)cc2)n(-c2cccc(N)c2)n1

Standard InChI:  InChI=1S/C20H22ClN5O/c1-20(2,3)17-12-18(26(25-17)16-6-4-5-14(22)11-16)24-19(27)23-15-9-7-13(21)8-10-15/h4-12H,22H2,1-3H3,(H2,23,24,27)

Standard InChI Key:  OOEIYCDNOQOFJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   15.8382    0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5133    0.4956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1742    0.9897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9064    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0823    1.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3294    2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1543    2.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9275    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9041    1.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0575    0.7040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3564    1.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6293    0.7492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3825    1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9282    1.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5255   -0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9519    2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2517    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5235    2.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4999    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2008    0.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8219    2.4855    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.8147   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8265   -1.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5476   -1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2582   -1.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2428   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9801   -1.9487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  6  7  1  0
  2 15  1  0
  2  3  1  0
 14 16  2  0
  6  8  1  0
 16 17  1  0
  3  4  2  0
 17 18  2  0
  6  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 14  1  0
  1 10  1  0
 18 21  1  0
  5  1  2  0
 15 22  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  4  6  1  0
 25 26  2  0
 26 15  1  0
 11 13  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA498947

   Pyrazolourea, 1a

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: 383.88

Molecular Weight (Monoisotopic): 383.1513

AlogP: 5.05

#Rotatable Bonds: 3

Polar Surface Area: 84.97

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.37

CX Basic pKa: 4.21

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -2.06

References

1. Getlik M, Grütter C, Simard JR, Klüter S, Rabiller M, Rode HB, Robubi A, Rauh D..  (2009)  Hybrid compound design to overcome the gatekeeper T338M mutation in cSrc.,  52  (13): [PMID:19462975] [10.1021/jm9002928]

2. Klüter S, Grütter C, Naqvi T, Rabiller M, Simard JR, Pawar V, Getlik M, Rauh D..  (2010)  Displacement assay for the detection of stabilizers of inactive kinase conformations.,  53  (1): [PMID:19928858] [10.1021/jm901297e]

3. Simard JR, Klüter S, Grütter C, Getlik M, Rabiller M, Rode HB, Rauh D..  (2009)  A new screening assay for allosteric inhibitors of cSrc.,  5  (6): [PMID:19396179] [10.1038/nchembio.162]

4. Richters A, Nguyen HD, Phan T, Simard JR, Grütter C, Engel J, Rauh D..  (2014)  Identification of type II and III DDR2 inhibitors.,  57  (10): [PMID:24754677] [10.1021/jm500167q]

5. Davies MP,Benitez R,Perez C,Jakupovic S,Welsby P,Rzepecka K,Alder J,Davidson C,Martinez A,Hayes JM.  (2021)  Structure-Based Design of Potent Selective Nanomolar Type-II Inhibitors of Glycogen Synthase Kinase-3β.,  64  (3.0): [PMID:33499592] [10.1021/acs.jmedchem.0c01568]

Source

Source(1):

• Scientific Literature