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

ID: ALA4160276

PubChem CID: 145958132

Max Phase: Preclinical

Molecular Formula: C24H26O4

Molecular Weight: 378.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H26O4/c1-23(2,3)16-12-10-15(11-13-16)18-14-24(4,26-5)28-21-17-8-6-7-9-19(17)27-22(25)20(18)21/h6-13,18H,14H2,1-5H3

Standard InChI Key:  AIMXYMVRWIFBRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   23.7201   -4.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1366   -4.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5486   -4.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2825   -6.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2814   -7.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9958   -7.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9941   -6.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7090   -6.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7124   -7.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4272   -7.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1432   -7.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4205   -6.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1352   -6.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8479   -6.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8520   -5.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4183   -5.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5593   -6.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5550   -7.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2667   -7.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9833   -7.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9836   -6.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2713   -6.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8596   -7.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3732   -4.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6964   -7.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6946   -8.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4115   -7.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4050   -8.1788    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
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4160276

   ---

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: 378.47

Molecular Weight (Monoisotopic): 378.1831

AlogP: 5.37

#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: 4.77

CX LogD: 4.77

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.56

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