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

ID: ALA4860741

PubChem CID: 164614341

Max Phase: Preclinical

Molecular Formula: C21H28N6

Molecular Weight: 364.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1cc(Nc2nc(N[C@@H](C)C3CCCCC3)nc3ccccc23)n[nH]1

Standard InChI:  InChI=1S/C21H28N6/c1-3-16-13-19(27-26-16)24-20-17-11-7-8-12-18(17)23-21(25-20)22-14(2)15-9-5-4-6-10-15/h7-8,11-15H,3-6,9-10H2,1-2H3,(H3,22,23,24,25,26,27)/t14-/m0/s1

Standard InChI Key:  GUNNUJMAJVZQNH-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

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   38.2897  -25.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2985  -24.2736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5875  -23.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5740  -25.5071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8625  -25.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8693  -24.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1578  -23.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4390  -24.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4361  -25.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1482  -25.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5931  -23.0291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3104  -22.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0584  -22.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6147  -22.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2070  -21.6385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3990  -21.8046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.4345  -22.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9240  -21.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0005  -25.5198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7186  -25.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4293  -25.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7259  -24.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4157  -26.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1224  -26.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8429  -26.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8523  -25.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1411  -25.1219    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  1  0
 21 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860741

   ---

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: 364.50

Molecular Weight (Monoisotopic): 364.2375

AlogP: 5.04

#Rotatable Bonds: 6

Polar Surface Area: 78.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.95

CX Basic pKa: 5.45

CX LogP: 5.76

CX LogD: 5.76

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -0.96

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