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

ID: ALA243001

Cas Number: 875258-85-8

PubChem CID: 23631116

Product Number: Y614914, Order Now?

Max Phase: Preclinical

Molecular Formula: C24H28FN3O2

Molecular Weight: 409.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccc(Oc3ccc(F)cc3)cc2c(=O)n1C[C@H]1CCCN(C(C)C)C1

Standard InChI:  InChI=1S/C24H28FN3O2/c1-16(2)27-12-4-5-18(14-27)15-28-17(3)26-23-11-10-21(13-22(23)24(28)29)30-20-8-6-19(25)7-9-20/h6-11,13,16,18H,4-5,12,14-15H2,1-3H3/t18-/m0/s1

Standard InChI Key:  FRKXOBMDEXCHHD-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  1  0  0  0  0  0999 V2000
    7.0137   -1.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7310   -2.1913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7271   -0.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0101   -0.9557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4429   -0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4391   -1.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1488   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8629   -1.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8627   -0.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1524   -0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268    0.2827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2948   -0.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0086    0.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0090    1.5177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2955    1.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7242    1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4379    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258    2.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5770   -0.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -0.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2893   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0031   -2.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7184   -1.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7153   -0.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0009   -0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4336   -2.1906    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001   -2.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 15 19  1  0
  3  4  1  0
 19 20  1  0
  9 10  2  0
 19 21  1  0
 10  5  1  0
  9 22  1  0
  1  2  2  0
 22 23  1  0
  3 11  2  0
 23 24  2  0
 24 25  1  0
  4 12  1  0
 25 26  2  0
  5  6  2  0
 26 27  1  0
 13 12  1  1
 27 28  2  0
 28 23  1  0
 13 14  1  0
 26 29  1  0
  1  4  1  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA243001

   YIL781

2. Alternative Forms:

   

   ALA243001

   YIL 781 hydrochloride

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: 409.51

Molecular Weight (Monoisotopic): 409.2166

AlogP: 4.76

#Rotatable Bonds: 5

Polar Surface Area: 47.36

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.14

CX LogP: 3.94

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.61

Np Likeness Score: -1.55

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. Hanrahan P, Bell J, Bottomley G, Bradley S, Clarke P, Curtis E, Davis S, Dawson G, Horswill J, Keily J, Moore G, Rasamison C, Bloxham J..  (2012)  Substituted azaquinazolinones as modulators of GHSr-1a for the treatment of type II diabetes and obesity.,  22  (6): [PMID:22342626] [10.1016/j.bmcl.2012.01.078]

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

4. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

5. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

6. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

7. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(4):

• Scientific Literature
• AstraZeneca Deposited Data
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6