Protodioscin
Basic information
- CAS
55056-80-9- Standard SMILES
C[C@H](CC[C@@]1(O)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]2[C@@H]1C)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
LVTJOONKWUXEFR-NCFOACLASA-N- Molecular formula
- C51H84O22
- Average molar mass
- 1,049.2 g/mol
- Monoisotopic mass
- 1,048.5454243
Overview
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.
Names & identifiers
- Preferred name
- Protodioscin
- IUPAC
- (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
- English name
- furostanol I
- Molecular formula
- C51H84O22
- Molecular weight
- 1049.21
Names & synonyms
Protodioscin55056-80-9D0LC3PH24PCHEBI:8588NSC698796(3beta,22R,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-[alpha-L-rhamnopyranosyl-(1->4)]-beta-D-glucopyranosideDTXSID901021361(3beta,22R,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-(alpha-L-rhamnopyranosyl-(1->4))-beta-D-glucopyranosideRefChem:46278DTXCID201506463beta-D-Glucopyranoside, (3beta,22beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1->4))-(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
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 346 Ų
- Hydrogen bond donors
- 13
- Hydrogen bond acceptors
- 22
- Rotatable bonds
- 14
- Heavy atoms
- 73
- Formal charge
- 0
- Complexity
- 1,900
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Furostanols and derivatives [ST0107]
Physicochemical properties
- Density
- 1.46 · 1.46±0.1 g/cm3(Predicted)
- pka
- 12 · 12+-.0.70(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Chemistry & industry
Additional notes
DefinitionChEBI: Protodioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-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 a metabolite. It is a steroid saponin, a trisaccharide derivative, a beta-D-glucoside, a pentacyclic triterpenoid and a cyclic hemiketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan.
Related reactions
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Compound notes
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