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

ID: ALA4875743

PubChem CID: 164628662

Max Phase: Preclinical

Molecular Formula: C19H18F2N8

Molecular Weight: 396.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(N[C@@H](C)c3ncc(F)cn3)nc3cccc(F)c23)n[nH]1

Standard InChI:  InChI=1S/C19H18F2N8/c1-3-12-7-15(29-28-12)26-18-16-13(21)5-4-6-14(16)25-19(27-18)24-10(2)17-22-8-11(20)9-23-17/h4-10H,3H2,1-2H3,(H3,24,25,26,27,28,29)/t10-/m0/s1

Standard InChI Key:  CNQINLDSXMBRHJ-JTQLQIEISA-N

Molfile:  

 
     RDKit          2D

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   21.3312  -23.0773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6202  -22.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6068  -24.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8952  -23.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9021  -23.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1906  -22.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4718  -23.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4690  -23.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1810  -24.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6259  -21.8329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3432  -21.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0911  -21.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6474  -21.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2397  -20.4423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4317  -20.6084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4672  -21.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9567  -20.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0332  -24.3235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7513  -23.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4621  -24.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4522  -25.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1620  -25.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8812  -25.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8859  -24.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1754  -23.9275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7587  -23.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1964  -21.8258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.5924  -25.5898    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
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  8  9  1  0
  9 10  2  0
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 13 14  2  0
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 17 18  1  0
  1 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 20 27  1  1
  7 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875743

   ---

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: 396.40

Molecular Weight (Monoisotopic): 396.1622

AlogP: 3.90

#Rotatable Bonds: 6

Polar Surface Area: 104.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.83

CX Basic pKa: 5.12

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.38

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