1,5-bis(4-ethoxyphenyl)penta-1,4-dien-3-one

ID: ALA1093989

PubChem CID: 668155

Max Phase: Preclinical

Molecular Formula: C21H22O3

Molecular Weight: 322.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(/C=C/C(=O)/C=C/c2ccc(OCC)cc2)cc1

Standard InChI:  InChI=1S/C21H22O3/c1-3-23-20-13-7-17(8-14-20)5-11-19(22)12-6-18-9-15-21(16-10-18)24-4-2/h5-16H,3-4H2,1-2H3/b11-5+,12-6+

Standard InChI Key:  HNLBEOUOQMIQHF-YDWXAUTNSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -0.9650    2.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    3.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722    3.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854    2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845    1.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5977    1.3783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3134    1.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0317    1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5537    2.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255    3.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662    3.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9822    2.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830    1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982    1.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4121    1.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6905    3.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287    1.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8410    1.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5576    1.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585    3.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1 13  1  0
 12 13  1  0
  6  7  1  0
 12 14  2  0
  3  4  2  0
 14 15  1  0
  7  8  2  0
 15 16  2  0
  8  3  1  0
 16 17  1  0
 17 18  2  0
  6  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 15  1  0
  9 10  1  0
 18 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 13 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093989

   (1E,4E)-1,5-bis(4-ethoxyphenyl)penta-1,4-dien-3-one

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: 322.40

Molecular Weight (Monoisotopic): 322.1569

AlogP: 4.78

#Rotatable Bonds: 8

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 5.22

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.09

References

1. Hu GX, Liang G, Chu Y, Li X, Lian QQ, Lin H, He Y, Huang Y, Hardy DO, Ge RS..  (2010)  Curcumin derivatives inhibit testicular 17beta-hydroxysteroid dehydrogenase 3.,  20  (8): [PMID:20346654] [10.1016/j.bmcl.2010.02.089]

2. Lin H, Hu GX, Guo J, Ge Y, Liang G, Lian QQ, Chu Y, Yuan X, Huang P, Ge RS..  (2013)  Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.,  23  (15): [PMID:23800686] [10.1016/j.bmcl.2013.05.080]

Source

Source(1):

• Scientific Literature