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

ID: ALA4876138

PubChem CID: 164628231

Max Phase: Preclinical

Molecular Formula: C21H20F2N6

Molecular Weight: 394.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCCc3ccc(F)cc3)nc3cccc(F)c23)n[nH]1

Standard InChI:  InChI=1S/C21H20F2N6/c1-2-15-12-18(29-28-15)26-20-19-16(23)4-3-5-17(19)25-21(27-20)24-11-10-13-6-8-14(22)9-7-13/h3-9,12H,2,10-11H2,1H3,(H3,24,25,26,27,28,29)

Standard InChI Key:  KFXDAXMJWYLKDE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.9397  -12.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9485  -11.3779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2375  -10.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2241  -12.6114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5124  -12.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5193  -11.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8078  -10.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0889  -11.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0861  -12.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7983  -12.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2432  -10.1334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9605   -9.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7085  -10.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2647   -9.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8571   -8.7427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0490   -8.9089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0846   -9.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5741   -8.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6505  -12.6241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3687  -12.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0794  -12.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7976  -12.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5062  -12.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2239  -12.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2317  -11.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5159  -11.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8012  -11.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9493  -11.0147    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8137  -10.1264    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 14 17  1  0
 17 18  1  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
  7 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876138

   ---

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: 394.43

Molecular Weight (Monoisotopic): 394.1718

AlogP: 4.59

#Rotatable Bonds: 7

Polar Surface Area: 78.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.94

CX Basic pKa: 5.24

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.46

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