(R)-3-((1-ethylpiperidin-3-yl)methyl)-2-o-tolyl-6-(trifluoromethoxy)quinazolin-4(3H)-one

ID: ALA396557

PubChem CID: 44428660

Max Phase: Preclinical

Molecular Formula: C24H26F3N3O2

Molecular Weight: 445.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCC[C@@H](Cn2c(-c3ccccc3C)nc3ccc(OC(F)(F)F)cc3c2=O)C1

Standard InChI:  InChI=1S/C24H26F3N3O2/c1-3-29-12-6-8-17(14-29)15-30-22(19-9-5-4-7-16(19)2)28-21-11-10-18(32-24(25,26)27)13-20(21)23(30)31/h4-5,7,9-11,13,17H,3,6,8,12,14-15H2,1-2H3/t17-/m1/s1

Standard InChI Key:  TYPWWUNYYCVRRR-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    7.6750  -24.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -25.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5246  -23.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9593  -23.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569  -22.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6750  -21.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1040  -21.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -22.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9621  -25.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467  -24.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333  -25.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341  -25.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542  -26.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9646  -25.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6808  -26.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2412  -23.4557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9535  -23.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6625  -24.2833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5384  -24.5848    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3733  -23.1617    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  1  0
 13 14  1  0
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  5 10  2  0
 14 18  1  0
  6  7  2  0
 18 19  1  0
  7  8  1  0
  4 20  2  0
  8  9  2  0
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  5  6  1  0
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  1 11  1  0
 23 24  2  0
 24 25  1  0
 12 11  1  6
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 26 21  1  0
  2 21  1  0
 12 13  1  0
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  1  2  1  0
  9 28  1  0
  1  4  1  0
 28 29  1  0
  2  3  2  0
 29 30  1  0
  3  6  1  0
 29 31  1  0
  5  4  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA396557

   (R)-3-((1-ethylpiperidin-3-yl)methyl)-2-o-tolyl-6-(trifluoromethoxy)quinazolin-4(3H)-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.49

Molecular Weight (Monoisotopic): 445.1977

AlogP: 5.00

#Rotatable Bonds: 5

Polar Surface Area: 47.36

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.88

CX LogP: 5.68

CX LogD: 4.19

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -1.29

References

1. Rudolph J, Esler WP, O'connor S, Coish PD, Wickens PL, Brands M, Bierer DE, Bloomquist BT, Bondar G, Chen L, Chuang CY, Claus TH, Fathi Z, Fu W, Khire UR, Kristie JA, Liu XG, Lowe DB, McClure AC, Michels M, Ortiz AA, Ramsden PD, Schoenleber RW, Shelekhin TE, Vakalopoulos A, Tang W, Wang L, Yi L, Gardell SJ, Livingston JN, Sweet LJ, Bullock WH..  (2007)  Quinazolinone derivatives as orally available ghrelin receptor antagonists for the treatment of diabetes and obesity.,  50  (21): [PMID:17887659] [10.1021/jm070071+]

Source

Source(1):

• Scientific Literature