ID: ALA255168

Max Phase: Preclinical

Molecular Formula: C21H24N2O

Molecular Weight: 320.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C)c1ccc(/C=C/C(=O)/C=C/c2ccc(N(C)C)cc2)cc1

Standard InChI:  InChI=1S/C21H24N2O/c1-22(2)19-11-5-17(6-12-19)9-15-21(24)16-10-18-7-13-20(14-8-18)23(3)4/h5-16H,1-4H3/b15-9+,16-10+

Standard InChI Key:  JWTSVUUPJIIXTO-KAVGSWPWSA-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: 320.44

Molecular Weight (Monoisotopic): 320.1889

AlogP: 4.11

#Rotatable Bonds: 6

Polar Surface Area: 23.55

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 5.03

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -0.13

References

1. Liang G, Li X, Chen L, Yang S, Wu X, Studer E, Gurley E, Hylemon PB, Ye F, Li Y, Zhou H..  (2008)  Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin.,  18  (4): [PMID:18234497] [10.1016/j.bmcl.2007.12.068]

2. 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]

3. Cui M, Ono M, Kimura H, Liu B, Saji H..  (2011)  Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for β-amyloid plaques.,  54  (7): [PMID:21417461] [10.1021/jm101404k]

4. Aher RB, Wanare G, Kawathekar N, Kumar RR, Kaushik NK, Sahal D, Chauhan VS..  (2011)  Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors.,  21  (10): [PMID:21493068] [10.1016/j.bmcl.2011.03.037]

5. 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]

6. Singh RS, Michel D, Das U, Dimmock JR, Alcorn J..  (2014)  Cytotoxic 1,5-diaryl-3-oxo-1,5-pentadienes: an assessment and comparison of membrane permeability using Caco-2 and MDCK monolayers.,  24  (22): [PMID:25442312] [10.1016/j.bmcl.2014.09.074]

7. 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]

8. Zhao F, Dong HH, Wang YH, Wang TY, Yan ZH, Yan F, Zhang DZ, Cao YY, Jin YS..  (2017)  Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp.,  8  (5): [PMID:30108820] [10.1039/C6MD00649C]

Source

Source(1):

• Scientific Literature