6-(butyl(methyl)amino)-2-(2-methoxyphenyl)-3-(piperidin-3-ylmethyl)quinazolin-4(3H)-one

ID: ALA390274

PubChem CID: 23630816

Max Phase: Preclinical

Molecular Formula: C26H34N4O2

Molecular Weight: 434.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN(C)c1ccc2nc(-c3ccccc3OC)n(CC3CCCNC3)c(=O)c2c1

Standard InChI:  InChI=1S/C26H34N4O2/c1-4-5-15-29(2)20-12-13-23-22(16-20)26(31)30(18-19-9-8-14-27-17-19)25(28-23)21-10-6-7-11-24(21)32-3/h6-7,10-13,16,19,27H,4-5,8-9,14-15,17-18H2,1-3H3

Standard InChI Key:  QTMCHHWITGOFQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.1279  -15.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107  -15.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146  -14.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316  -14.6932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987  -14.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026  -15.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072  -15.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7212  -15.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210  -14.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0107  -14.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149  -13.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8469  -14.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8484  -13.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331  -13.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327  -12.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461  -11.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616  -12.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5637  -13.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415  -15.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353  -14.2800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500  -14.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349  -13.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643  -14.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5789  -14.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932  -14.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5534  -15.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2665  -15.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2652  -16.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5448  -17.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347  -16.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172  -17.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057  -16.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  5  3  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
  1 19  1  0
  3  4  1  0
  9 20  1  0
  9 10  2  0
 20 21  1  0
 10  5  1  0
 20 22  1  0
  1  2  2  0
 21 23  1  0
  3 11  2  0
 23 24  1  0
 24 25  1  0
  4 12  1  0
 19 26  2  0
  5  6  2  0
 26 27  1  0
 13 12  1  0
 27 28  2  0
 13 14  1  0
 28 29  1  0
  1  4  1  0
 29 30  2  0
 30 19  1  0
  6  7  1  0
 30 31  1  0
  2  6  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA390274

   6-[Butyl(methyl)amino]-2-(2-methoxyphenyl)-3-(piperidin-3-ylmethyl)quinazolin-4-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: 434.58

Molecular Weight (Monoisotopic): 434.2682

AlogP: 4.31

#Rotatable Bonds: 8

Polar Surface Area: 59.39

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.22

CX LogP: 4.27

CX LogD: 1.59

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.57

Np Likeness Score: -1.09

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