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

ID: ALA4858397

PubChem CID: 164610953

Max Phase: Preclinical

Molecular Formula: C21H21FN6

Molecular Weight: 376.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(NCCc3ccc(F)cc3)nc3ccccc23)n[nH]1

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

Standard InChI Key:  LADJEJIWLZWLBM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   11.9394   -5.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9482   -4.6609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2372   -4.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2238   -5.8945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -5.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5190   -4.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8075   -4.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887   -4.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0858   -5.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7980   -5.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2428   -3.4165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9601   -3.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7081   -3.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2644   -2.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8567   -2.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0487   -2.1920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0843   -2.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5738   -2.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6502   -5.9071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3683   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0790   -5.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7972   -5.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5057   -5.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2234   -5.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2313   -4.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5155   -4.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8008   -4.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9489   -4.2977    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
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4858397

   ---

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: 12.96

CX Basic pKa: 5.48

CX LogP: 5.39

CX LogD: 5.38

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.45

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