(S)-N4-(5-ethyl-1H-pyrazol-3-yl)-7-fluoro-N2-(1-(4-fluorophenyl)ethyl)quinazoline-2,4-diamine

ID: ALA4860927

PubChem CID: 164612547

Max Phase: Preclinical

Molecular Formula: C21H20F2N6

Molecular Weight: 394.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(N[C@@H](C)c3ccc(F)cc3)nc3cc(F)ccc23)n[nH]1

Standard InChI:  InChI=1S/C21H20F2N6/c1-3-16-11-19(29-28-16)26-20-17-9-8-15(23)10-18(17)25-21(27-20)24-12(2)13-4-6-14(22)7-5-13/h4-12H,3H2,1-2H3,(H3,24,25,26,27,28,29)/t12-/m0/s1

Standard InChI Key:  KEIROKXBRBGGGJ-LBPRGKRZSA-N

Molfile:  

 
     RDKit          2D

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   41.0544  -11.2155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3433  -10.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3299  -12.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6183  -12.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6251  -11.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9136  -10.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1948  -11.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1919  -12.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9040  -12.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3490   -9.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0663   -9.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8143   -9.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3706   -9.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9630   -8.5805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.1549   -8.7465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.1905   -9.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6800   -8.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7564  -12.4619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4745  -12.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1853  -12.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4819  -11.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1754  -13.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8853  -13.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6045  -13.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6093  -12.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8988  -12.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3159  -13.7281    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.4762  -12.4376    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  1 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  1
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 25 28  1  0
  9 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860927

   ---

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: 5.11

#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: 12.91

CX Basic pKa: 4.90

CX LogP: 5.66

CX LogD: 5.66

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -1.49

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