ST 29:1;O;Hex;FA 16:0
Basic information
- CAS
18749-71-8- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OCC1OC(OC2CCC3(C)C(=CCC4C3CCC3(C)C(C(C)CCC(CC)C(C)C)CCC43)C2)C(O)C(O)C1O- InChIKey
JCLYMCVRBRHEHI-UHFFFAOYSA-N- Molecular formula
- C51H90O7
- Average molar mass
- 815.3 g/mol
- Monoisotopic mass
- 814.66865521
Overview
CID 13051622 has been reported in Asparagus gobicus, Acer mandshuricum, and Pistia stratiotes with data available.
Names & identifiers
- Preferred name
- ST 29:1;O;Hex;FA 16:0
- IUPAC
- [6-[[17-(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]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate
- English name
- Sitosteryl (6'-O-palmitoyl)-3-β-D-glucopyranoside
- Molecular formula
- C51H90O7
- Molecular weight
- 815.27
Names & synonyms
ST 29:1;O;Hex;FA 16:0Esterified Steryl GlucosidesTAA74971[6-[[17-(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]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate6-naphthalen-2-ylamino-1H-pyrimidine-2,4-dione;Sitosteryl (6/'-O-palmitoyl)-3-beta-D-glucopyranosideSitoindoside ISitoindoside-O-palmitoyl)-3-β-D-glucopyranosidebeta-Sitosterol glucoside 6'-O-monopalmitatebeta-Sitosteryl beta-D-glucoside monopalmitatebeta-Sitosteryl-beta-D-glucoside-6-monopalmitate
Show more names
Stigmast-5-en-3-beta-6'-palmitoylglucopyranosideSitosteryl (6-O-palmitoyl)-3-β-D-glucopyranosideSitosteryl (6'-O-palmitoyl)-3-β-D-glucopyranosideSitosteryl (6'-O-palmitoyl)-3beta-D-glucopyranoside
Properties
Computed structural properties
- XLogP
- 15.1
- Topological polar surface area
- 105 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 25
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 1,250
Experimental & physicochemical properties
Melting Point163 - 165 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 163 · 163-165 °C
- Boiling point
- 811.2 · 811.2±65.0 °C(Predicted)
- Density
- 1.05 · 1.05±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- form
- powder
- pka
- 12.83 · 12.83±0.70(Predicted)
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
UsesSitoindoside I was isolated as a potent cytotoxic agent from latex and soybeans and showed in vitro inhibitory effects on proliferation of various cancer cell lines.
Additional notes
DefinitionChEBI: Sitoindoside I is a steroid saponin that is sitosterol attached to a 6-O-hexadecanoyl-beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from Breynia fruticosa. It has a role as a plant metabolite. It is a fatty acid ester, a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a hexadecanoic acid and a sitosterol. It derives from a hydride of a stigmastane.
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