(E)-3-(3,5-Dimethoxyphenyl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one

ID: ALA3125821

PubChem CID: 71523683

Max Phase: Preclinical

Molecular Formula: C18H18O5

Molecular Weight: 314.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)c2cc(OC)ccc2O)cc(OC)c1

Standard InChI:  InChI=1S/C18H18O5/c1-21-13-5-7-18(20)16(11-13)17(19)6-4-12-8-14(22-2)10-15(9-12)23-3/h4-11,20H,1-3H3/b6-4+

Standard InChI Key:  GUNJFYJQOLVLTF-GQCTYLIASA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   11.3856  -19.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3845  -20.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0925  -21.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8022  -20.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7993  -19.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0907  -19.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5105  -21.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5118  -21.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2176  -20.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9259  -21.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6330  -20.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0923  -21.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3401  -21.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0466  -20.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0458  -19.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3325  -19.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6288  -19.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0883  -18.7126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7948  -18.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3283  -18.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7548  -21.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7557  -21.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0339  -18.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
  3 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
  6 18  1  0
 18 19  1  0
 16 20  1  0
 14 21  1  0
 21 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3125821

   (e)-1-(2-Hydroxy-5-methoxyphenyl)-3-(3',5'-dimethoxyphenyl)prop-2-en-1-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: 314.34

Molecular Weight (Monoisotopic): 314.1154

AlogP: 3.31

#Rotatable Bonds: 6

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: 0.25

References

1. Shin SY, Jung H, Ahn S, Hwang D, Yoon H, Hyun J, Yong Y, Cho HJ, Koh D, Lee YH, Lim Y..  (2014)  Polyphenols bearing cinnamaldehyde scaffold showing cell growth inhibitory effects on the cisplatin-resistant A2780/Cis ovarian cancer cells.,  22  (6): [PMID:24565968] [10.1016/j.bmc.2014.01.058]

2. Lee DY, Lee DH, Jung JY, Koh D, Kim GS, Ahn YS, Lee YH, Lim Y, Shin SY..  (2016)  A synthetic chalcone derivative, 2-hydroxy-3',5,5'-trimethoxychalcone (DK-139), suppresses the TNFα-induced invasive capability of MDA-MB-231 human breast cancer cells by inhibiting NF-κB-mediated GROα expression.,  26  (1): [PMID:26602275] [10.1016/j.bmcl.2015.10.094]

3. Gil HN, Koh D, Lim Y, Lee YH, Shin SY..  (2018)  The synthetic chalcone derivative 2-hydroxy-3',5,5'-trimethoxychalcone induces unfolded protein response-mediated apoptosis in A549 lung cancer cells.,  28  (17): [PMID:30017320] [10.1016/j.bmcl.2018.07.003]

Source

Source(1):

• Scientific Literature