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

ID: ALA4168631

PubChem CID: 145953675

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2CC(C)(OC)Oc3c2c(=O)oc2ccccc32)cc1

Standard InChI:  InChI=1S/C21H20O5/c1-21(24-3)12-16(13-8-10-14(23-2)11-9-13)18-19(26-21)15-6-4-5-7-17(15)25-20(18)22/h4-11,16H,12H2,1-3H3

Standard InChI Key:  UHDUKYUECUHRSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   32.4763   -4.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8924   -5.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3042   -4.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0408   -6.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0395   -7.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7534   -8.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7516   -6.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4660   -6.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4694   -7.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1836   -8.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8991   -7.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1769   -6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8911   -6.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6032   -6.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6074   -5.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1748   -5.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3140   -6.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3097   -7.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0208   -8.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7368   -7.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7371   -6.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0255   -6.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6148   -8.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1280   -4.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4494   -8.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4475   -8.8706    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4168631

   ---

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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 4.08

#Rotatable Bonds: 3

Polar Surface Area: 57.90

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: 0.72

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