ID: ALA472887

Max Phase: Preclinical

Molecular Formula: C24H26O5

Molecular Weight: 394.47

Molecule Type: Small molecule

Representations

Synonyms (1): Go-Y032
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(/C=C2\CCC/C(=C\c3ccc(OC)c(OC)c3)C2=O)cc1OC

Standard InChI:  InChI=1S/C24H26O5/c1-26-20-10-8-16(14-22(20)28-3)12-18-6-5-7-19(24(18)25)13-17-9-11-21(27-2)23(15-17)29-4/h8-15H,5-7H2,1-4H3/b18-12+,19-13+

Standard InChI Key:  YOTDZZKBJHGVNA-KLCVKJMQSA-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: 394.47

Molecular Weight (Monoisotopic): 394.1780

AlogP: 4.94

#Rotatable Bonds: 6

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.13

References

1. 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]

2. Yamakoshi H, Ohori H, Kudo C, Sato A, Kanoh N, Ishioka C, Shibata H, Iwabuchi Y..  (2010)  Structure-activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof.,  18  (3): [PMID:20060305] [10.1016/j.bmc.2009.12.045]

3. 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]

4. Lam KW, Tham CL, Liew CY, Syahida A, Abdul Rahman MB, Israf DA, Lajis NH.  (2012)  Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives,  21  (3): [10.1007/s00044-010-9521-0]

5. Bayomi SM, El-Kashef HA, El-Ashmawy MB, Nasr MNA, El-Sherbeny MA, Badria FA, Abou-zeid LA, Ghaly MA, Abdel-Aziz NI.  (2013)  Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents,  22  (3): [10.1007/s00044-012-0116-9]

6. Leow PC, Bahety P, Boon CP, Lee CY, Tan KL, Yang T, Ee PL..  (2014)  Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.,  71  [PMID:24275249] [10.1016/j.ejmech.2013.10.073]

7. Tan KL, Ali A, Du Y, Fu H, Jin HX, Chin TM, Khan M, Go ML..  (2014)  Synthesis and evaluation of bisbenzylidenedioxotetrahydrothiopranones as activators of endoplasmic reticulum (ER) stress signaling pathways and apoptotic cell death in acute promyelocytic leukemic cells.,  57  (14): [PMID:24960549] [10.1021/jm401352a]

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. Leong SW, Chia SL, Abas F, Yusoff K..  (2018)  Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro.,  157  [PMID:30138803] [10.1016/j.ejmech.2018.08.039]

10. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]

Source

Source(1):

• Scientific Literature