N2-(1-(4-chlorophenyl)cyclopropyl)-N4-(5-ethyl-1H-pyrazol-3-yl)quinazoline-2,4-diamine

ID: ALA4876835

PubChem CID: 164626831

Max Phase: Preclinical

Molecular Formula: C22H21ClN6

Molecular Weight: 404.91

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NC3(c4ccc(Cl)cc4)CC3)nc3ccccc23)n[nH]1

Standard InChI:  InChI=1S/C22H21ClN6/c1-2-16-13-19(29-28-16)25-20-17-5-3-4-6-18(17)24-21(26-20)27-22(11-12-22)14-7-9-15(23)10-8-14/h3-10,13H,2,11-12H2,1H3,(H3,24,25,26,27,28,29)

Standard InChI Key:  APFHTWKIILPSJZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   29.9869  -14.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4036  -15.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8159  -14.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9762  -15.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9850  -14.4481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2739  -14.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2606  -15.6815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5490  -15.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5559  -14.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8443  -14.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1256  -14.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1227  -15.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8348  -15.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2797  -13.2036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9970  -12.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7448  -13.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3011  -12.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8935  -11.8131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0854  -11.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1209  -12.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6105  -11.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6869  -15.6942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1158  -15.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1059  -16.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8158  -16.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5349  -16.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5396  -15.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8291  -15.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2462  -16.9605    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 15  2  0
 17 20  1  0
 20 21  1  0
  4 22  1  0
 22  2  1  0
  2 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876835

   ---

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: 404.91

Molecular Weight (Monoisotopic): 404.1516

AlogP: 5.41

#Rotatable Bonds: 6

Polar Surface Area: 78.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.90

CX Basic pKa: 5.37

CX LogP: 5.95

CX LogD: 5.95

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.21

References

1. Uehling DE, Joseph B, Chung KC, Zhang AX, Ler S, Prakesch MA, Poda G, Grouleff J, Aman A, Kiyota T, Leung-Hagesteijn C, Konda JD, Marcellus R, Griffin C, Subramaniam R, Abibi A, Strathdee CA, Isaac MB, Al-Awar R, Tiedemann RE..  (2021)  Design, Synthesis, and Characterization of 4-Aminoquinazolines as Potent Inhibitors of the G Protein-Coupled Receptor Kinase 6 (GRK6) for the Treatment of Multiple Myeloma.,  64  (15.0): [PMID:34291633] [10.1021/acs.jmedchem.1c00506]

2. Tesmer, John J G JJ, Tesmer, Valerie M VM, Lodowski, David T DT, Steinhagen, Henning H and Huber, Jochen J.  2010-02-25  Structure of human G protein-coupled receptor kinase 2 in complex with the kinase inhibitor balanol.  [PMID:20128603]

Source

Source(1):

• Scientific Literature