ID: ALA271295

Max Phase: Preclinical

Molecular Formula: C29H38N2O3

Molecular Weight: 462.63

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C)CCCOc1ccc(/C=C2\CC/C(=C\c3ccc(OCCCN(C)C)cc3)C2=O)cc1

Standard InChI:  InChI=1S/C29H38N2O3/c1-30(2)17-5-19-33-27-13-7-23(8-14-27)21-25-11-12-26(29(25)32)22-24-9-15-28(16-10-24)34-20-6-18-31(3)4/h7-10,13-16,21-22H,5-6,11-12,17-20H2,1-4H3/b25-21+,26-22+

Standard InChI Key:  AKERQZTUCNLYPR-CDTUYSNOSA-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: 462.63

Molecular Weight (Monoisotopic): 462.2882

AlogP: 5.18

#Rotatable Bonds: 12

Polar Surface Area: 42.01

Molecular Species: BASE

HBA: 5

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 9.56

CX LogP: 4.99

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -0.40

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. 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. Wang Y, Xiao J, Zhou H, Yang S, Wu X, Jiang C, Zhao Y, Liang D, Li X, Liang G..  (2011)  A novel monocarbonyl analogue of curcumin, (1E,4E)-1,5-bis(2,3-dimethoxyphenyl)penta-1,4-dien-3-one, induced cancer cell H460 apoptosis via activation of endoplasmic reticulum stress signaling pathway.,  54  (11): [PMID:21504179] [10.1021/jm200017g]

4. 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]

Source

Source(1):

• Scientific Literature