(R)-(+)-6-(4-Methylnaphthalen-1-yl)-5,6-dihydro-2Hpyran-2-one

ID: ALA502569

PubChem CID: 44570286

Max Phase: Preclinical

Molecular Formula: C16H14O2

Molecular Weight: 238.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc([C@H]2CC=CC(=O)O2)c2ccccc12

Standard InChI:  InChI=1S/C16H14O2/c1-11-9-10-14(13-6-3-2-5-12(11)13)15-7-4-8-16(17)18-15/h2-6,8-10,15H,7H2,1H3/t15-/m1/s1

Standard InChI Key:  PCEBRNJCKGIJLD-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   13.4792   -6.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1996   -6.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1964   -5.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9099   -5.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6232   -5.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3345   -5.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3347   -4.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6174   -4.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8998   -4.4386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6161   -3.1977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7653   -6.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7667   -5.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4761   -5.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4729   -4.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7610   -4.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0509   -4.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0576   -5.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0491   -6.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4  3  1  6
  8 10  2  0
  4  5  1  0
 11 12  2  0
  1  2  2  0
 11  1  1  0
 12 13  1  0
  2  3  1  0
 13 14  1  0
  3 13  2  0
 14 15  2  0
 15 16  1  0
  4  9  1  0
 16 17  2  0
 17 12  1  0
  5  6  1  0
 11 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA502569

   (2R)-2-(4-methylnaphthalen-1-yl)-2,3-dihydropyran-6-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: 238.29

Molecular Weight (Monoisotopic): 238.0994

AlogP: 3.69

#Rotatable Bonds: 1

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.71

Np Likeness Score: 1.26

References

1. Kasaplar P, Yilmazer O, Cağir A..  (2009)  6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: asymmetric synthesis, and anti-proliferative properties.,  17  (1): [PMID:19022676] [10.1016/j.bmc.2008.10.069]

2. Kanbur T, Kara M, Kutluer M, Şen A, Delman M, Alkan A, Otaş HO, Akçok İ, Çağır A..  (2017)  CRM1 inhibitory and antiproliferative activities of novel 4'-alkyl substituted klavuzon derivatives.,  25  (16): [PMID:28689976] [10.1016/j.bmc.2017.06.030]

3. Delman M, Avcı ST, Akçok İ, Kanbur T, Erdal E, Çağır A..  (2019)  Antiproliferative activity of (R)-4'-methylklavuzon on hepatocellular carcinoma cells and EpCAM⁺/CD133⁺ cancer stem cells via SIRT1 and Exportin-1 (CRM1) inhibition.,  180  [PMID:31306909] [10.1016/j.ejmech.2019.07.024]

Source

Source(1):

• Scientific Literature