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

ID: ALA4163231

PubChem CID: 145958995

Max Phase: Preclinical

Molecular Formula: C21H20O4

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H20O4/c1-13-8-10-14(11-9-13)16-12-21(2,23-3)25-19-15-6-4-5-7-17(15)24-20(22)18(16)19/h4-11,16H,12H2,1-3H3

Standard InChI Key:  RPOKSBKRVVZBBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   15.7054   -4.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1216   -4.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5333   -4.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2695   -6.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2684   -7.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9823   -7.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9804   -6.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6949   -6.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6983   -7.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4127   -7.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1282   -7.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4059   -6.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1202   -6.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8324   -6.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8365   -5.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4038   -5.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5434   -6.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5390   -7.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2503   -7.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9663   -7.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9667   -6.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2548   -6.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8440   -7.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3573   -4.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6789   -7.8147    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
M  END

Alternative Forms

1. Parent:

   

   ALA4163231

   ---

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: 336.39

Molecular Weight (Monoisotopic): 336.1362

AlogP: 4.38

#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: 3.74

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: 0.66

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