(S)-N4-(3-Ethyl-1H-pyrazol-5-yl)-N2-(1-(5-fluoropyridin-2-yl)-ethyl)-5-methylquinazoline-2,4-diamine

ID: ALA4875929

PubChem CID: 164629101

Max Phase: Preclinical

Molecular Formula: C21H22FN7

Molecular Weight: 391.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(N[C@@H](C)c3ccc(F)cn3)nc3cccc(C)c23)n[nH]1

Standard InChI:  InChI=1S/C21H22FN7/c1-4-15-10-18(29-28-15)26-20-19-12(2)6-5-7-17(19)25-21(27-20)24-13(3)16-9-8-14(22)11-23-16/h5-11,13H,4H2,1-3H3,(H3,24,25,26,27,28,29)/t13-/m0/s1

Standard InChI Key:  AZCHQQLGTDJHFL-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.8390  -13.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8478  -12.5772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1368  -12.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1233  -13.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4118  -13.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4187  -12.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7072  -12.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9884  -12.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9856  -13.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6976  -13.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1425  -11.3328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8598  -10.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6077  -11.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1639  -10.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7563   -9.9423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9482  -10.1084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9838  -10.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4733  -10.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5497  -13.8235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2678  -13.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9786  -13.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2753  -12.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9687  -14.6591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6785  -15.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3977  -14.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4025  -13.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6920  -13.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1089  -15.0896    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7130  -11.3258    0.0000 C   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
 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
  7 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875929

   ---

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: 391.45

Molecular Weight (Monoisotopic): 391.1921

AlogP: 4.67

#Rotatable Bonds: 6

Polar Surface Area: 91.41

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: 5.91

CX LogP: 5.04

CX LogD: 5.03

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.36

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