ID: ALA477054

Max Phase: Preclinical

Molecular Formula: C23H26O7

Molecular Weight: 414.45

Molecule Type: Small molecule

Representations

Synonyms (1): Go-Y016
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(/C=C/C(=O)/C=C/c2cc(OC)c(OC)c(OC)c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C23H26O7/c1-25-18-11-15(12-19(26-2)22(18)29-5)7-9-17(24)10-8-16-13-20(27-3)23(30-6)21(14-16)28-4/h7-14H,1-6H3/b9-7+,10-8+

Standard InChI Key:  QMBQAUFXKZCNOT-FIFLTTCUSA-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: 414.45

Molecular Weight (Monoisotopic): 414.1679

AlogP: 4.03

#Rotatable Bonds: 10

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: 3.88

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: 0.30

References

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2. Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H..  (2009)  Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted.,  44  (5): [PMID:18584918] [10.1016/j.ejmech.2008.05.010]

3. 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]

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. Qiu X, Du Y, Lou B, Zuo Y, Shao W, Huo Y, Huang J, Yu Y, Zhou B, Du J, Fu H, Bu X..  (2010)  Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway.,  53  (23): [PMID:21070043] [10.1021/jm1004545]

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. Li Q, Chen J, Luo S, Xu J, Huang Q, Liu T..  (2015)  Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues.,  93  [PMID:25728027] [10.1016/j.ejmech.2015.02.005]

9. Francisco KR, Monti L, Yang W, Park H, Liu LJ, Watkins K, Amarasinghe DK, Nalli M, Roberto Polaquini C, Regasini LO, Eduardo Miller Crotti A, Silvestri R, Guidi Magalhães L, Caffrey CR..  (2023)  Structure-activity relationship of dibenzylideneacetone analogs against the neglected disease pathogen, Trypanosoma brucei.,  81  [PMID:36608774] [10.1016/j.bmcl.2023.129123]

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