ID: ALA387599

Max Phase: Preclinical

Molecular Formula: C26H30O7

Molecular Weight: 454.52

Molecule Type: Small molecule

Representations

Synonyms (1): 2,6-Bis(3,4,5-Trimethoxybenzylidene)Cyclohexanone
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(/C=C2\CCC/C(=C\c3cc(OC)c(OC)c(OC)c3)C2=O)cc(OC)c1OC

Standard InChI:  InChI=1S/C26H30O7/c1-28-20-12-16(13-21(29-2)25(20)32-5)10-18-8-7-9-19(24(18)27)11-17-14-22(30-3)26(33-6)23(15-17)31-4/h10-15H,7-9H2,1-6H3/b18-10+,19-11+

Standard InChI Key:  OXIWSGTZUCVQPH-XOBNHNQQSA-N

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

Properties

Molecular Weight: 454.52

Molecular Weight (Monoisotopic): 454.1992

AlogP: 4.96

#Rotatable Bonds: 8

Polar Surface Area: 72.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -0.01

References

1. Das U, Kawase M, Sakagami H, Ideo A, Shimada J, Molnár J, Baráth Z, Bata Z, Dimmock JR..  (2007)  3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity.,  15  (10): [PMID:17383883] [10.1016/j.bmc.2007.03.022]

2. Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S..  (2009)  Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents.,  17  (6): [PMID:19243951] [10.1016/j.bmc.2008.10.044]

3. Singh N, Pandey J, Yadav A, Chaturvedi V, Bhatnagar S, Gaikwad AN, Sinha SK, Kumar A, Shukla PK, Tripathi RP..  (2009)  A facile synthesis of alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations.,  44  (4): [PMID:18952325] [10.1016/j.ejmech.2008.09.026]

4. 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]

5. Yadav B, Taurin S, Rosengren RJ, Schumacher M, Diederich M, Somers-Edgar TJ, Larsen L..  (2010)  Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin.,  18  (18): [PMID:20728364] [10.1016/j.bmc.2010.07.063]

6. Wei X, Du ZY, Zheng X, Cui XX, Conney AH, Zhang K..  (2012)  Synthesis and evaluation of curcumin-related compounds for anticancer activity.,  53  [PMID:22551677] [10.1016/j.ejmech.2012.04.005]

7. 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]

8. Deck LM, Hunsaker LA, Vander Jagt TA, Whalen LJ, Royer RE, Vander Jagt DL..  (2018)  Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.,  143  [PMID:29223100] [10.1016/j.ejmech.2017.11.048]

9. Din ZU, Trapp MA, Soman de Medeiros L, Lazarin-Bidóia D, Garcia FP, Peron F, Nakamura CV, Rodríguez IC, Wadood A, Rodrigues-Filho E..  (2018)  Symmetrical and unsymmetrical substituted 2,5-diarylidene cyclohexanones as anti-parasitic compounds.,  155  [PMID:29920454] [10.1016/j.ejmech.2018.06.031]

10. Moreira J, Durães F, Freitas-Silva J, Szemerédi N, Resende DISP, Pinto E, da Costa PM, Pinto M, Spengler G, Cidade H, Sousa E..  (2022)  New diarylpentanoids and chalcones as potential antimicrobial adjuvants.,  67  [PMID:35447343] [10.1016/j.bmcl.2022.128743]

Source

Source(1):

• Scientific Literature