ContaminantDB: Stevioside

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 00:47:06 UTC

Update Date

2016-11-09 01:18:47 UTC

Accession Number

CHEM028903

Identification

Common Name

Stevioside

Class

Small Molecule

Description

Constituent of Stevia rebaudiana (stevia). Sweetening agent which is 300 times sweeter than sucrose. Stevia rebaudiana is extensively cultivated in Japan, and Stevioside is a permitted sweetener in that country Rebaudioside B, D, and E may also be present in minute quantities; however, it is suspected that rebaudioside B is a byproduct of the isolation technique. The two majority compounds stevioside and rebaudioside, primarily responsible for the sweet taste of stevia leaves, were first isolated by two French chemists in 1931.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Diterpene glycoside	HMDB
Eupatorin?	HMDB
Rebaudin	HMDB
Stevin?	HMDB
Steviosin	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid	Generator
Stevioside	MeSH
Steviol glycoside	MeSH

Chemical Formula

C₃₈H₆₀O₁₈

Average Molecular Mass

804.872 g/mol

Monoisotopic Mass

804.378 g/mol

CAS Registry Number

57817-89-7

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Traditional Name

stevioside

SMILES

CC12CCCC(C)(C1CCC13CC(=C)C(C1)(CCC23)OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3

InChI Key

UEDUENGHJMELGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Substituents

Steviol glycoside
Diterpenoid
Kaurane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.51 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	294.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	186.15 m³·mol⁻¹	ChemAxon
Polarizability	83.95 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-0103809210-618c8917bf91bf14e0da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-040r-0104904000-6810fe906f79bdcb23c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02w9-0415902100-c4cc22c8df7fa9e745e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fic-1402569430-00c6ad06eb887c4431b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1911715300-ccd331e4189584049205	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-4901410000-d567568eafd4a9c77616	Spectrum