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

ID: ALA4159847

PubChem CID: 145956370

Max Phase: Preclinical

Molecular Formula: C21H17F3O4

Molecular Weight: 390.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H17F3O4/c1-20(26-2)11-15(12-7-9-13(10-8-12)21(22,23)24)17-18(28-20)14-5-3-4-6-16(14)27-19(17)25/h3-10,15H,11H2,1-2H3

Standard InChI Key:  GWUBTJJHKYQLFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.6558  -12.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0719  -13.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4838  -12.8781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198  -15.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186  -16.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326  -16.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9308  -14.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453  -15.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6487  -16.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631  -16.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0786  -16.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563  -14.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0706  -15.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7829  -14.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7871  -14.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542  -14.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4938  -15.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4895  -16.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2008  -16.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9169  -16.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9172  -15.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2053  -14.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7945  -16.4830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3078  -12.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6295  -16.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6277  -17.3205    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3442  -16.0862    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3377  -16.9050    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
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4159847

   ---

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: 390.36

Molecular Weight (Monoisotopic): 390.1079

AlogP: 5.09

#Rotatable Bonds: 2

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 0.36

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