Structure Database (LMSD)
Common Name
fucosterol
Systematic Name
(24E)-stigmasta-5,24(28)-dien-3β-ol
Synonyms
- (24E)-24-n-propylidenecholesterol
- (3beta,24E)-stigmasta-5,24(28)-dien-3-ol
- (E)-stigmasta-5,24(28)-dien-3beta-ol
- 24E-ethylidene-cholest-5-en-3beta-ol
- fucosterin
- trans-24-ethylidenecholesterol
3D model of fucosterol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Fucosterol is a plant sterol found in algae that has diverse biological activities including antioxidant, anti-inflammatory, anticancer, and antidiabetic properties among others.1 It decreases markers of oxidative damage and increases antioxidative enzyme activity in vitro.2 It reduces the expression of TNF-α and IL-6 following LPS administration by halting NF-κB and p38 MAPK signaling in RAW 264.7 murine macrophages.3 In HEK293, MCF-7, and SiHa cells, fucosterol decreases proliferation (IC50s = 185.4, 43.3, and 34.0 µg/ml, respectively).4 It also has anticancer activity in HL-60 leukemia cells, where it inhibits cell growth, halts the cell cycle at the G2/M transition, and induces apoptosis with maximally increased caspase-9, -8, and -3 expression at 68.8 µM.5 In a streptozotocin rat model of diabetes, it decreases serum glucose concentrations when administered at 30 mg/kg.6
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
OSELKOCHBMDKEJ-JUGJNGJRSA-N
InChi (Click to copy)
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES (Click to copy)
C1C[C@H](O)CC2=CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])([C@@H](CC/C(=C\C)/C(C)C)C)CC[C@]13[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
464.33
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
8.23
Molar Refractivity
128.70
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Created at
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Updated at
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