REBAUDIOSIDE A (CHEM007393)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:25:03 UTC
Update Date2016-11-09 01:09:55 UTC
Accession NumberCHEM007393
Identification
Common NameREBAUDIOSIDE A
ClassSmall Molecule
DescriptionA rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13-[(2-O-beta-D-Glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid beta-D-glucopyranosyl esterChEBI
19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acidChEBI
19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosylsteviolChEBI
Reb aChEBI
Reb-aChEBI
Rebaudioside-aChEBI
SteviaChEBI
Sweetener 4g-SChEBI
13-[(2-O-b-D-Glucopyranosyl-3-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate b-D-glucopyranosyl esterGenerator
13-[(2-O-b-D-Glucopyranosyl-3-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid b-D-glucopyranosyl esterGenerator
13-[(2-O-beta-D-Glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate beta-D-glucopyranosyl esterGenerator
13-[(2-O-Β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate β-D-glucopyranosyl esterGenerator
13-[(2-O-Β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid β-D-glucopyranosyl esterGenerator
19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosyl-13-hydroxykaur-16-en-19-OateGenerator
19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acidGenerator
19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-OateGenerator
19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosyl-13-hydroxykaur-16-en-19-OateGenerator
19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acidGenerator
19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosylsteviolGenerator
19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosylsteviolGenerator
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-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 acidHMDB
Stevioside a3HMDB
Rebaudioside AMeSH
Chemical FormulaC44H70O23
Average Molecular Mass967.021 g/mol
Monoisotopic Mass966.431 g/mol
CAS Registry Number58543-16-1
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate
Traditional Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate
SMILES[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(=O)[C@]2(C)CCC[C@@]3(C)[C@]4([H])CC[C@@]5(C[C@]4(CC5=C)CC[C@]23[H])O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]2([H])O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]1([H])O
InChI IdentifierInChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,41-,42-,43-,44+/m1/s1
InChI KeyHELXLJCILKEWJH-NCGAPWICSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentSteviol glycosides
Alternative Parents
Substituents
  • Steviol glycoside
  • Oligosaccharide
  • Diterpenoid
  • Kaurane diterpenoid
  • Fatty acyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acyl
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.4 g/LALOGPS
logP-1.4ALOGPS
logP-3.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area374.13 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity218.56 m³·mol⁻¹ChemAxon
Polarizability94.86 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-0uxr-0000000079-75402eef616f2b12831cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-0udi-0000000090-fb46c72609f54077cf9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 60V, negativesplash10-0udl-0001206090-44ebe132417d2ec16d00Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 80V, negativesplash10-00or-0004903000-5f4f5ef5cb14a46c0404Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0003407944-099a80a1866d9d12a98aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0016-0105609510-c96697836b2d1aafe2caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0114219321-3f7bdf66df4e62b9d735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ftk-0301406869-401b87bfebcf28e217d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tj-0810517978-553fcbc8360b4f975878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2912405030-6a11a761d8d227a3bcf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0000001269-f47808f99d3ef6acf100Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8300001397-f498c720bf4e6a9aacd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-5100009231-030e605dab68d0397f94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-0101608955-231c87c74fb5ee2e0ca3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ktf-2627409455-184dd1d1d8afaa68067fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9803304652-6890556b9fa860d144f5Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034950
FooDB IDFDB013543
Phenol Explorer IDNot Available
KNApSAcK IDC00023175
BiGG IDNot Available
BioCyc IDCPD-14506
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRebaudioside_A
Chemspider ID5294031
ChEBI ID145012
PubChem Compound ID6918840
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15610349
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25353385
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26776281
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=27352150
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=27638403
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28218969
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29262312
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29355553
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=29433626
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29461634
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=29655729
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=30291959
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=30666114
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=30883860
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31030274
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=31159256
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=31324778
18.
19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
20. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
21. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
23. Pilz RB, Willis RC, Boss GR: The influence of ribose 5-phosphate availability on purine synthesis of cultured human lymphoblasts and mitogen-stimulated lymphocytes. J Biol Chem. 1984 Mar 10;259(5):2927-35.
24. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
25. The lipid handbook with CD-ROM