2-Methoxy-2-methyl-(4-(4-fluorophenyl))-3,4-dihydropyrano[3,2-c]chromen-5(2H)-one

ID: ALA4162161

PubChem CID: 145959701

Max Phase: Preclinical

Molecular Formula: C20H17FO4

Molecular Weight: 340.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1(C)CC(c2ccc(F)cc2)c2c(c3ccccc3oc2=O)O1

Standard InChI:  InChI=1S/C20H17FO4/c1-20(23-2)11-15(12-7-9-13(21)10-8-12)17-18(25-20)14-5-3-4-6-16(14)24-19(17)22/h3-10,15H,11H2,1-2H3

Standard InChI Key:  YQFRGWIKSKDUKH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   41.1561   -3.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5721   -4.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9840   -3.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7205   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7193   -6.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4332   -7.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4314   -5.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1458   -6.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1492   -6.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8634   -7.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5789   -6.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8566   -5.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5708   -6.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2830   -5.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2871   -4.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8545   -4.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9938   -6.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9894   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7006   -7.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4166   -6.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4169   -6.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7052   -5.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2946   -7.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8078   -3.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1292   -7.2561    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  2  0
 12 16  1  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  2 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
 11 23  2  0
  3 24  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4162161

   ---

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: 340.35

Molecular Weight (Monoisotopic): 340.1111

AlogP: 4.21

#Rotatable Bonds: 2

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 0.46

References

1. Rayar AM, Lagarde N, Martin F, Blanchard F, Liagre B, Ferroud C, Zagury JF, Montes M, Sylla-Iyarreta Veitía M..  (2018)  New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling.,  146  [PMID:29407982] [10.1016/j.ejmech.2018.01.054]

2. Rayar AM, Lagarde N, Martin F, Blanchard F, Liagre B, Ferroud C, Zagury JF, Montes M, Sylla-Iyarreta Veitía M..  (2018)  New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling.,  146  [PMID:29407982] [10.1016/j.ejmech.2018.01.054]

Source

Source(1):

• Scientific Literature