5-fluoro-4-(2-(isoxazol-3-yl)hydrazinyl)-N-phenethylquinazolin-2-amine

ID: ALA4860235

PubChem CID: 164618085

Max Phase: Preclinical

Molecular Formula: C19H16FN5O

Molecular Weight: 349.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Fc1cccc2nc(NCCc3ccccc3)nc(Nc3ccon3)c12

Standard InChI:  InChI=1S/C19H16FN5O/c20-14-7-4-8-15-17(14)18(23-16-10-12-26-25-16)24-19(22-15)21-11-9-13-5-2-1-3-6-13/h1-8,10,12H,9,11H2,(H2,21,22,23,24,25)

Standard InChI Key:  MSSPUQWXXCTHAQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    9.2873  -13.1960    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6586  -15.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9929  -14.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7070  -14.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9500  -14.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5637  -15.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6616  -14.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4139  -14.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2420  -15.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2814  -14.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2399  -14.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9861  -15.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6936  -15.6687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7127  -13.2030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8260  -15.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2718  -15.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667  -14.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9497  -15.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1119  -15.6815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5326  -15.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4052  -15.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4232  -12.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1646  -13.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7156  -12.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3118  -11.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5114  -11.9850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0
 16 12  1  0
 21  8  2  0
  2  7  2  0
 18  2  1  0
 15 20  1  0
  5 11  2  0
  8  4  1  0
 17  6  1  0
 10 17  2  0
  4  3  2  0
 10  1  1  0
 11  9  1  0
 12  3  1  0
 21 19  1  0
  4 14  1  0
  9 18  2  0
  9 20  1  0
 19 15  1  0
 12 13  2  0
  3 10  1  0
  6 16  2  0
 13 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860235

   ---

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: 349.37

Molecular Weight (Monoisotopic): 349.1339

AlogP: 4.16

#Rotatable Bonds: 6

Polar Surface Area: 75.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: 5.20

CX LogP: 4.73

CX LogD: 4.70

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -1.60

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