REBAUDIOSIDE A (CED0008407)

Record Information
Version1.0
Creation Date2016-05-19 02:25:03 UTC
Update Date2026-05-14 19:48:29 UTC
Accession NumberCHEM007393
Identification
Common NameREBAUDIOSIDE A
ClassSmall Molecule
Description
REBAUDIOSIDE A is a chemical compound with the formula C44H70O23. REBAUDIOSIDE A belongs to the terpene glycosides, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 967.02 g/mol, REBAUDIOSIDE A is a heavy molecule. In industrial applications, this compound is used as a flavouring, nutrient, softener, and conditioner. It has been recorded in three sources, including building and construction materials such as tents or canopies, as well as electrical and electronic equipment including antennas and amplifiers.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-0uxr-0000000079-75402eef616f2b12831cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000090-fb46c72609f54077cf9fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-0001206090-44ebe132417d2ec16d00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0004903000-5f4f5ef5cb14a46c0404Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0003407944-099a80a1866d9d12a98aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0016-0105609510-c96697836b2d1aafe2caNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0114219321-3f7bdf66df4e62b9d735Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ftk-0301406869-401b87bfebcf28e217d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01tj-0810517978-553fcbc8360b4f975878Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2912405030-6a11a761d8d227a3bcf9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gb9-0000001269-f47808f99d3ef6acf100Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-8300001397-f498c720bf4e6a9aacd1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-007c-5100009231-030e605dab68d0397f94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06rl-0101608955-231c87c74fb5ee2e0ca3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ktf-2627409455-184dd1d1d8afaa68067fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9803304652-6890556b9fa860d144f5Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)2.95827
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)1.79053
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)1.79053
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)1.47914
Coagulation factor X structureClick to view 3D structureCoagulation factor XP00742HumansPredicted (SEA)490.294
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)4.98235
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)17.1268
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)533.034
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)3.89246
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)3.19182
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)2.25763
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)13.935
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)15.6477
Click to view 3D structureSolute carrier organic anion transporter family member 1B2Q9QZX8Rattus norvegicusPredicted (SEA)4.67095
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)2058.02
Tyrosine-protein phosphatase non-receptor type 2 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 2P17706HumansPredicted (SEA)428.326
Click to view 3D structureHemagglutininB4URE7Influenza A virusPredicted (SEA)6.69503
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)3.73676
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)2020.89
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)2768.16
Coagulation factor XI structureClick to view 3D structureCoagulation factor XIP03951HumansPredicted (SEA)1213.36
Galectin-9 structureClick to view 3D structureGalectin-9O00182HumansPredicted (SEA)31.996
Urokinase-type plasminogen activator structureClick to view 3D structureUrokinase-type plasminogen activatorP00749HumansPredicted (SEA)1820.19
FUN14 domain-containing protein 1 structureClick to view 3D structureFUN14 domain-containing protein 1Q8IVP5HumansPredicted (SEA)7.55137
Tissue-type plasminogen activator structureClick to view 3D structureTissue-type plasminogen activatorP00750HumansPredicted (SEA)1879.28
Concentrations
Not Available
External Links
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