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Protodioscin

CAT: 0804-HY-N0799-03Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0799-03Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Protodioscin, a major steroidal saponin in Trigonella foenum-graecum Linn., has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties.
CAS Number
55056-80-9
UNSPSC
12352005
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Protodioscin.html
Purity
99.64
Solubility
DMSO : 50 mg/mL (ultrasonic) |H2O : 50 mg/mL (ultrasonic)
Smiles
C[C@@]1([C@]([C@@H]2C)([H])[C@](O[C@]2(O)CC[C@@H](C)CO[C@@H]([C@@H]([C@@H](O)[C@@H]3O)O)O[C@@H]3CO)([H])C4)[C@]4([H])[C@@](CC=C5[C@@]6(CC[C@H](O[C@@](O[C@H](CO)[C@@H](O[C@@](O[C@@H](C)[C@H](O)[C@H]7O)([H])[C@@H]7O)[C@@H]8O)([H])[C@@H]8O[C@@](O[C@@H](C)[C@H](O)[C@H]9O)([H])[C@@H]9O)C5)C)([H])[C@]6([H])CC1
Molecular Formula
C51H84O22
Molecular Weight
1049.20
References & Citations
[1]Shen J, et al. Protodioscin ameliorates fructose-induced renal injury via inhibition of the mitogen activated protein kinase pathway. Phytomedicine. 2016 Nov 15;23 (12) :1504-1510.|[2]Zhang X, et al. Potential neuroprotection of protodioscin against cerebral ischemia-reperfusion injury in rats through intervening inflammation and apoptosis. Steroids. 2016 Sep;113:52-63|[3]Wang T, et al. Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica. Planta Med. 2010 Oct;76 (15) :1642-6
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

Protodioscin

Protodioscin is a furostanol glycoside that consists of the trisaccharide alpha-L-Rha-(14)-[alpha-L-Rha-(12)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as an antineoplastic agent, an antilipemic drug, a neuroprotective agent, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a beta-D-glucoside, a pentacyclic triterpenoid, a cyclic hemiketal, a steroid saponin and a trisaccharide derivative. It derives from a hydride of a furostan.

CAS Number55056-80-9
PubChem CID441891
IUPAC Name(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Molecular FormulaC51H84O22
Molecular Weight1049.2
XLogP-1.3
Topological Polar Surface Area346
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count22
Rotatable Bond Count14
Heavy Atom Count73
Formal Charge0
Complexity1900
SMILES
C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
InChI
InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1
InChIKey
LVTJOONKWUXEFR-UEZXSUPNSA-N
Chemical Structure
2D Structure
2D structure of Protodioscin
CAS: 55056-80-9
CID: 441891
Formula: C51H84O22
MW: 1049.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1049.2
XLogP3-1.3
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count22
Rotatable Bond Count14
Exact Mass1048.54542430
Monoisotopic Mass1048.54542430
Topological Polar Surface Area346 Ų
Heavy Atom Count73
Formal Charge0
Complexity1900
Isotope Atom Count0
Defined Atom Stereocenter Count31
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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