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

ID: ALA4876072

PubChem CID: 164627432

Max Phase: Preclinical

Molecular Formula: C21H21FN6

Molecular Weight: 376.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCCc3ccccc3)nc3cccc(F)c23)n[nH]1

Standard InChI:  InChI=1S/C21H21FN6/c1-2-15-13-18(28-27-15)25-20-19-16(22)9-6-10-17(19)24-21(26-20)23-12-11-14-7-4-3-5-8-14/h3-10,13H,2,11-12H2,1H3,(H3,23,24,25,26,27,28)

Standard InChI Key:  SKFBRLBWFBITTM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   22.7437  -12.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7525  -11.5609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0415  -11.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0280  -12.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3165  -12.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3234  -11.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6118  -11.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8930  -11.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8901  -12.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6022  -12.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0471  -10.3166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7644   -9.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5124  -10.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0687   -9.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6610   -8.9259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8529   -9.0921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8885   -9.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3781   -9.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4544  -12.8072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1726  -12.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8834  -12.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6015  -12.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3100  -12.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0277  -12.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0356  -11.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3198  -11.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6050  -11.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6177  -10.3095    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
  7 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876072

   ---

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: 376.44

Molecular Weight (Monoisotopic): 376.1812

AlogP: 4.45

#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: 5.39

CX LogD: 5.38

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.36

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