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

ID: ALA4860406

PubChem CID: 164616025

Max Phase: Preclinical

Molecular Formula: C22H23FN6O

Molecular Weight: 406.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(N[C@@H](C)c3ccc(F)cc3)nc3ccc(OC)cc23)n[nH]1

Standard InChI:  InChI=1S/C22H23FN6O/c1-4-16-11-20(29-28-16)26-21-18-12-17(30-3)9-10-19(18)25-22(27-21)24-13(2)14-5-7-15(23)8-6-14/h5-13H,4H2,1-3H3,(H3,24,25,26,27,28,29)/t13-/m0/s1

Standard InChI Key:  GEGGWFUNXFASDQ-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

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   21.1116  -19.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4006  -19.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3872  -20.7246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6755  -20.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6824  -19.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9709  -19.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2520  -19.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2492  -20.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9614  -20.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4063  -18.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   21.8716  -18.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4278  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0203  -16.8559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2122  -17.0220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2478  -17.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7373  -17.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8137  -20.7373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5318  -20.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2426  -20.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5392  -19.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2327  -21.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9427  -21.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6618  -21.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6666  -20.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9561  -20.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3732  -22.0036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.5397  -19.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5442  -18.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 19  1  0
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 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
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860406

   ---

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: 406.47

Molecular Weight (Monoisotopic): 406.1917

AlogP: 4.98

#Rotatable Bonds: 7

Polar Surface Area: 87.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: 5.47

CX LogP: 5.36

CX LogD: 5.35

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -1.37

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