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

ID: ALA4173939

PubChem CID: 145949539

Max Phase: Preclinical

Molecular Formula: C20H17NO6

Molecular Weight: 367.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1(C)CC(c2ccc([N+](=O)[O-])cc2)c2c(c3ccccc3oc2=O)O1

Standard InChI:  InChI=1S/C20H17NO6/c1-20(25-2)11-15(12-7-9-13(10-8-12)21(23)24)17-18(27-20)14-5-3-4-6-16(14)26-19(17)22/h3-10,15H,11H2,1-2H3

Standard InChI Key:  CHMLOTQPCCPPLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   17.3554  -12.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7715  -13.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1832  -12.3930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9198  -14.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9187  -15.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6324  -16.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6306  -14.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3451  -14.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3484  -15.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0627  -16.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7781  -15.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0559  -14.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7702  -14.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4822  -14.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4864  -13.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0538  -13.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1931  -14.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1888  -15.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8999  -16.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6158  -15.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6162  -14.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9045  -14.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4938  -15.9972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0071  -12.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3338  -16.0123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0482  -15.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3318  -16.8361    0.0000 O   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
 25 26  2  0
 25 27  1  0
 20 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4173939

   ---

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: 367.36

Molecular Weight (Monoisotopic): 367.1056

AlogP: 3.98

#Rotatable Bonds: 3

Polar Surface Area: 91.81

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: 0.33

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]

Source

Source(1):

• Scientific Literature