3-Benzo[1,3]dioxol-5-yl-5-(4-methoxyphenyl)-6-carbethoxy-2-cyclohexen-1-one

ID: ALA2272749

PubChem CID: 71570509

Max Phase: Preclinical

Molecular Formula: C23H22O6

Molecular Weight: 394.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1C(=O)C=C(c2ccc3c(c2)OCO3)CC1c1ccc(OC)cc1

Standard InChI:  InChI=1S/C23H22O6/c1-3-27-23(25)22-18(14-4-7-17(26-2)8-5-14)10-16(11-19(22)24)15-6-9-20-21(12-15)29-13-28-20/h4-9,11-12,18,22H,3,10,13H2,1-2H3

Standard InChI Key:  FCNGMGUVBPEVNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    4.3290   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -2.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241   -2.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290   -1.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -1.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -2.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753   -2.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -4.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -4.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -4.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7753   -4.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -4.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9591   -4.8411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4393   -4.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9591   -3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1778   -3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1778   -4.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4645   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7554   -3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7554   -4.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4645   -4.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  1  7  2  0
  8  9  2  0
 11 12  1  0
 10 11  1  0
  8 10  1  0
  6  8  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  1  0
 16 19  1  0
  5 13  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 25  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 25 29  2  0
 24 26  2  0
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272749

   Ethyl 4-(1,3-benzodioxol-5-yl)-6-(4-methoxyphenyl)-2-oxocyclohex-3-ene-1-carboxylate

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: 394.42

Molecular Weight (Monoisotopic): 394.1416

AlogP: 3.74

#Rotatable Bonds: 5

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.53

CX Basic pKa: ┄

CX LogP: 4.13

CX LogD: 4.13

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: 0.13

References

1. Shakil NA, Singh MK, Sathiyendiran M, Kumar J, Padaria JC..  (2013)  Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives.,  59  [PMID:23229055] [10.1016/j.ejmech.2012.10.038]

Source

Source(1):

• Scientific Literature