1,3-Bis-(2,4-dimethoxy-phenyl)-propenone

ID: ALA140130

Cas Number: 79004-62-9

PubChem CID: 5720640

Max Phase: Preclinical

Molecular Formula: C19H20O5

Molecular Weight: 328.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2',4,4',6-Tetramethoxychalcone | 79004-62-9|(2E)-1,3-bis(2,4-dimethoxyphenyl)prop-2-en-1-one|(E)-1,3-bis(2,4-dimethoxyphenyl)prop-2-en-1-one|2-Propen-1-one, 1,3-bis(2,4-dimethoxyphenyl)-, (2E)-|2',4,4',6-Tetramethoxychalcone|MLS001048852|CHEMBL140130|SCHEMBL2462049|HMS2270D11|MFCD00812734|AKOS001333097|UPCMLD0ENAT5725037:001|SMR000387059|VU0013725-4|AB00080393-01|AB00080393-09|SR-01000204293|SR-01000204293-1|Z46029788|F3139-0777

Canonical SMILES:  COc1ccc(/C=C/C(=O)c2ccc(OC)cc2OC)c(OC)c1

Standard InChI:  InChI=1S/C19H20O5/c1-21-14-7-5-13(18(11-14)23-3)6-10-17(20)16-9-8-15(22-2)12-19(16)24-4/h5-12H,1-4H3/b10-6+

Standard InChI Key:  SSDJNESHQBSBBC-UXBLZVDNSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -4.3473  -14.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3484  -15.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336  -16.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172  -15.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200  -14.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354  -14.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071  -14.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911  -14.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2102  -13.5228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782  -14.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622  -14.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622  -15.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6530  -15.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3669  -15.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611  -14.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454  -14.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760  -15.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911  -15.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835  -15.9794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877  -16.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632  -16.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7774  -15.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020  -16.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008  -16.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
 12 17  1  0
 17 18  1  0
  7  9  2  0
 14 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
  2 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
  4 23  1  0
  5  6  2  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA140130

   (2E)-1,3-bis(2,4-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: 328.36

Molecular Weight (Monoisotopic): 328.1311

AlogP: 3.62

#Rotatable Bonds: 7

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -0.02

References

1. Liu M, Wilairat P, Go ML..  (2001)  Antimalarial alkoxylated and hydroxylated chalcones [corrected]: structure-activity relationship analysis.,  44  (25): [PMID:11728189] [10.1021/jm0101747]

2. Nowakowska Z..  (2007)  A review of anti-infective and anti-inflammatory chalcones.,  42  (2): [PMID:17112640] [10.1016/j.ejmech.2006.09.019]

3. Liu XL, Tee HW, Go ML..  (2008)  Functionalized chalcones as selective inhibitors of P-glycoprotein and breast cancer resistance protein.,  16  (1): [PMID:17964170] [10.1016/j.bmc.2007.10.006]

4. Boumendjel A, Boccard J, Carrupt PA, Nicolle E, Blanc M, Geze A, Choisnard L, Wouessidjewe D, Matera EL, Dumontet C..  (2008)  Antimitotic and antiproliferative activities of chalcones: forward structure-activity relationship.,  51  (7): [PMID:18293907] [10.1021/jm0708331]

5. Bandgar BP, Gawande SS, Bodade RG, Totre JV, Khobragade CN..  (2010)  Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents.,  18  (3): [PMID:20064725] [10.1016/j.bmc.2009.11.066]

6. PubChem BioAssay data set, 

7. Valdameri G, Gauthier C, Terreux R, Kachadourian R, Day BJ, Winnischofer SM, Rocha ME, Frachet V, Ronot X, Di Pietro A, Boumendjel A..  (2012)  Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity.,  55  (7): [PMID:22449016] [10.1021/jm2016528]

8. Cai CY, Rao L, Rao Y, Guo JX, Xiao ZZ, Cao JY, Huang ZS, Wang B..  (2017)  Analogues of xanthones--Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates.,  130  [PMID:28242551] [10.1016/j.ejmech.2017.02.007]

9. Qin HL, Zhang ZW, Lekkala R, Alsulami H, Rakesh KP..  (2020)  Chalcone hybrids as privileged scaffolds in antimalarial drug discovery: A key review.,  193  [PMID:32179331] [10.1016/j.ejmech.2020.112215]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays