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Daucosterol

CAT: 0804-HY-N0410-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0410-01Size:5 mg
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Description
Daucosterol is an orally active natural sterol compound, which has anti-inflammatory, anticancer and immunomodulatory activities. Daucosterol inhibits cancer cell proliferation by inducing autophagy through ROS-dependent manner. Daucosterol also inhibits colon cancer growth by inducing apoptosis, inhibiting cell migration and invasion and targeting caspase signalling pathway[1][2][3].
CAS Number
474-58-8
Product Name Alternative
Eleutheroside A; β-Sitosterol β-D-glucoside
UNSPSC
12352005
Hazard Statement
H302-H315-H319-H335
Target
Apoptosis; Autophagy; Reactive Oxygen Species (ROS)
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Daucosterol.html
Purity
93.98
Solubility
DMSO : 3.33 mg/mL (ultrasonic)
Smiles
C[C@H](CC[C@@H](CC)C(C)C)[C@](CC1)([H])[C@]2(C)[C@]1([H])[C@]([C@]3([H])CC2)([H])CC=C([C@]3(C)CC4)C[C@H]4O[C@@]5([H])[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5
Molecular Formula
C35H60O6
Molecular Weight
576.85
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
References & Citations
[1]Jiang LH, et al. Daucosterol protects neurons against oxygen-glucose deprivation/reperfusion-mediated injury by activating IGF1 signaling pathway. J Steroid Biochem Mol Biol. 2015 Aug;152:45-52.|[2]Zhao C, et al. Daucosterol inhibits cancer cell proliferation by inducing autophagy through reactive oxygen species-dependent manner. Life Sci. 2015 Sep 15;137:37-43. |[3]Gao P, et al. Daucosterol induces autophagic-dependent apoptosis in prostate cancer via JNK activation. Biosci Trends. 2019 May 12;13 (2) :160-167. |[4]Wang GQ, et al. Daucosterol inhibits colon cancer growth by inducing apoptosis, inhibiting cell migration and invasion and targeting caspase signalling pathway. Bangladesh Journal of Pharmacolog, 2016, 11 (2) : 395-401.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Sitogluside

Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a beta-D-glucoside, a steroid saponin and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane.

CAS Number474-58-8
PubChem CID5742590
IUPAC Name(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC35H60O6
Molecular Weight576.8
XLogP7.7
Topological Polar Surface Area99.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Heavy Atom Count41
Formal Charge0
Complexity920
SMILES
CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)C(C)C
InChI
InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24+,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1
InChIKey
NPJICTMALKLTFW-OFUAXYCQSA-N
Chemical Structure
2D Structure
2D structure of Sitogluside
CAS: 474-58-8
CID: 5742590
Formula: C35H60O6
MW: 576.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight576.8
XLogP37.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass576.43898963
Monoisotopic Mass576.43898963
Topological Polar Surface Area99.4 Ų
Heavy Atom Count41
Formal Charge0
Complexity920
Isotope Atom Count0
Defined Atom Stereocenter Count14
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
GTR19170711-01Daucosterol

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