6-(4-chlorophenyl)-3-{[(3S)-1-isopropylpiperidin-3-yl]methyl}-2-methylquinazolin-4(3H)-one

ID: ALA244936

PubChem CID: 23631387

Max Phase: Preclinical

Molecular Formula: C24H28ClN3O

Molecular Weight: 409.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccc(-c3ccc(Cl)cc3)cc2c(=O)n1C[C@H]1CCCN(C(C)C)C1

Standard InChI:  InChI=1S/C24H28ClN3O/c1-16(2)27-12-4-5-18(14-27)15-28-17(3)26-23-11-8-20(13-22(23)24(28)29)19-6-9-21(25)10-7-19/h6-11,13,16,18H,4-5,12,14-15H2,1-3H3/t18-/m0/s1

Standard InChI Key:  ARLXUYKHWSHMLR-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    8.3262  -17.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0435  -18.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0396  -16.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3226  -17.0515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7554  -17.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7516  -17.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4613  -18.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1754  -17.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1752  -17.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4649  -16.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0393  -15.8131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6073  -16.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6057  -15.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3211  -15.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3215  -14.5781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6080  -14.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925  -14.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904  -15.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8895  -16.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6020  -17.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3158  -16.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3158  -15.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5961  -15.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8853  -15.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0295  -15.4029    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0367  -14.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7504  -14.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0383  -13.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6126  -18.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  6  7  1  0
  2  6  1  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
  9 19  1  0
  3  4  1  0
 19 20  2  0
  9 10  2  0
 20 21  1  0
 10  5  1  0
 21 22  2  0
  1  2  2  0
 22 23  1  0
  3 11  2  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
  4 12  1  0
 15 26  1  0
  5  6  2  0
 26 27  1  0
 13 12  1  1
 26 28  1  0
 13 14  1  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA244936

   6-(4-chlorophenyl)-3-{[(3S)-1-isopropylpiperidin-3-yl]methyl}-2-methylquinazolin-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: 409.96

Molecular Weight (Monoisotopic): 409.1921

AlogP: 5.15

#Rotatable Bonds: 4

Polar Surface Area: 38.13

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.15

CX LogP: 4.55

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.46

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+]

2. McCoull W, Barton P, Broo A, Brown AJH, Clarke DS, Coope G, Davies RDM, Dossetter AG, Kelly EE, Knerr L, MacFaul P, Holmes JL, Martin N, Moore JE, Morgan D, Newton C, Osterlund K, Robb GR, Rosevere E, Selmi N, Stokes S, Svensson TS, Ullah VBK, Williams EJ.  (2013)  Identification of pyrazolo-pyrimidinones as GHS-R1a antagonists and inverse agonists for the treatment of obesity,  4  (2): [10.1039/C2MD20340E]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data