(S)-N4-(5-ethyl-1H-pyrazol-3-yl)-6-fluoro-N2-(1-(4-fluorophenyl)ethyl)quinazoline-2,4-diamine

ID: ALA4860226

PubChem CID: 164613737

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)nc3ccc(F)cc23)n[nH]1

Standard InChI:  InChI=1S/C21H20F2N6/c1-3-16-11-19(29-28-16)26-20-17-10-15(23)8-9-18(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:  OXTUEPHEEDUGGB-LBPRGKRZSA-N

Molfile:  

 
     RDKit          2D

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    4.2397  -18.9024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287  -18.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154  -20.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037  -19.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106  -18.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991  -18.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803  -18.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774  -19.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895  -20.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344  -17.6580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2517  -17.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9996  -17.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5559  -16.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483  -16.2674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402  -16.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757  -17.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8652  -16.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9416  -20.1486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6598  -19.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706  -20.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672  -18.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607  -20.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0706  -21.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897  -20.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7944  -20.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839  -19.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5009  -21.4149    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6680  -18.4677    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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  9 10  2  0
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 17 18  1  0
  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
  8 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860226

   ---

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: 4.54

CX LogP: 5.66

CX LogD: 5.66

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -1.47

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