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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:53:02 UTC
Update Date2022-07-19 22:09:52 UTC
HMDB IDHMDB0034950
Secondary Accession Numbers
  • HMDB34950
Metabolite Identification
Common NameRebaudioside A
DescriptionRebaudioside A 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. Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae), which is a member of the sunflower family native to Paraguay and Brazil.  Steviol glycosides are the main ingredients (or precursors) of many sweeteners marketed under the generic name stevia and several other trade names. Stevia is widely used as a non-nutritive replacement for common sugar (sucrose). Rebaudioside A is one of the major sweetening constituents of commercial stevia. Stevia leaves typically contain 9.1% stevioside and 3.8% rebaudioside A (by dry weight) as the two major sweeteners (PMID: 19961353 ). Rebaudioside A is the sweetest and most stable steviol glycoside. Rebaudioside A was first isolated by two French chemists (Bridel and Lavielle) in 1931. A recent evaluation found rebaudoside A to be about 240 times sweeter, and stevioside about 140 times sweeter than sucrose (PMID: 17397883 ). Rebaudioside A also had the least bitterness and aftertaste of all steviol glycosides (PMID: 19961353 ). Rebaudioside A binds to the T1R2 and T1R3 (sweet) receptors as well as the T2R4 and T2R14 (bitter) receptors (PMID: 24705770 ).  Rebaudioside A is not an endogenously occurring human metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rebaudioside A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults or impacts from environmental, dietary and occupational sources.
Structure
Data?1583514603
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 Weight967.021
Monoisotopic Molecular Weight966.430788514
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
CAS Registry Number58543-16-1
SMILES
[H][C@@]1(O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@@]34C[C@]5(CC3=C)CC[C@]3([H])[C@@](C)(CCC[C@@]3(C)[C@]5([H])CC4)C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point242 - 244 °CNot Available
Boiling Point1103.45 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1253 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.428 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-312.31130932474
DeepCCS[M+Na]+286.11630932474
AllCCS[M+H]+283.932859911
AllCCS[M+H-H2O]+284.632859911
AllCCS[M+NH4]+283.232859911
AllCCS[M+Na]+283.032859911
AllCCS[M-H]-287.032859911
AllCCS[M+Na-2H]-292.432859911
AllCCS[M+HCOO]-298.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 20V, negative-QTOFsplash10-0uxr-0000000079-75402eef616f2b12831c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 40V, negative-QTOFsplash10-0udi-0000000090-fb46c72609f54077cf9f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 60V, negative-QTOFsplash10-0udl-0001206090-44ebe132417d2ec16d002020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 80V, negative-QTOFsplash10-00or-0004903000-5f4f5ef5cb14a46c04042020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 10V, Positive-QTOFsplash10-000i-0003407944-099a80a1866d9d12a98a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 20V, Positive-QTOFsplash10-0016-0105609510-c96697836b2d1aafe2ca2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 40V, Positive-QTOFsplash10-0006-0114219321-3f7bdf66df4e62b9d7352016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 10V, Negative-QTOFsplash10-0ftk-0301406869-401b87bfebcf28e217d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 20V, Negative-QTOFsplash10-01tj-0810517978-553fcbc8360b4f9758782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 40V, Negative-QTOFsplash10-004i-2912405030-6a11a761d8d227a3bcf92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 10V, Negative-QTOFsplash10-0gb9-0000001269-f47808f99d3ef6acf1002021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 20V, Negative-QTOFsplash10-0a4i-8300001397-f498c720bf4e6a9aacd12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 40V, Negative-QTOFsplash10-007c-5100009231-030e605dab68d0397f942021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 10V, Positive-QTOFsplash10-06rl-0101608955-231c87c74fb5ee2e0ca32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 20V, Positive-QTOFsplash10-0ktf-2627409455-184dd1d1d8afaa68067f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside A 40V, Positive-QTOFsplash10-0a4i-9803304652-6890556b9fa860d144f52021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013543
KNApSAcK IDC00023175
Chemspider ID5294031
KEGG Compound IDNot Available
BioCyc IDCPD-14506
BiGG IDNot Available
Wikipedia LinkRebaudioside_A
METLIN IDNot Available
PubChem Compound6918840
PDB IDNot Available
ChEBI ID145012
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1600541
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:6699001 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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. [PubMed:16902246 ]
  4. 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. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Brandle JE, Telmer PG: Steviol glycoside biosynthesis. Phytochemistry. 2007 Jul;68(14):1855-63. doi: 10.1016/j.phytochem.2007.02.010. Epub 2007 Mar 29. [PubMed:17397883 ]
  7. Risso D, Morini G, Pagani L, Quagliariello A, Giuliani C, De Fanti S, Sazzini M, Luiselli D, Tofanelli S: Genetic signature of differential sensitivity to stevioside in the Italian population. Genes Nutr. 2014 May;9(3):401. doi: 10.1007/s12263-014-0401-y. Epub 2014 Apr 6. [PubMed:24705770 ]
  8. Goyal SK, Samsher, Goyal RK: Stevia (Stevia rebaudiana) a bio-sweetener: a review. Int J Food Sci Nutr. 2010 Feb;61(1):1-10. doi: 10.3109/09637480903193049. [PubMed:19961353 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in G-protein coupled receptor activity
Specific function:
Gustducin-coupled receptor for denatonium and N(6)- propyl-2-thiouracil implicated in the perception of bitter compounds in the oral cavity and the gastrointestinal tract. Signals through PLCB2 and the calcium-regulated cation channel TRPM5. In airway epithelial cells, binding of denatonium increases the intracellular calcium ion concentration and stimulates ciliary beat frequency
Gene Name:
TAS2R4
Uniprot ID:
Q9NYW5
Molecular weight:
33840.2
General function:
Involved in G-protein coupled receptor activity
Specific function:
Putative taste receptor. TAS1R1/TAS1R3 responds to the umami taste stimulus (the taste of monosodium glutamate). TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners. TAS1R3 is essential for the recognition and response to the disaccharide trehalose. Sequence differences within and between species can significantly influence the selectivity and specificity of taste responses
Gene Name:
TAS1R3
Uniprot ID:
Q7RTX0
Molecular weight:
93385.2
General function:
Involved in G-protein coupled receptor activity
Specific function:
Putative taste receptor. TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners
Gene Name:
TAS1R2
Uniprot ID:
Q8TE23
Molecular weight:
95182.5
General function:
Not Available
Specific function:
Receptor that may play a role in the perception of bitterness and is gustducin-linked. May play a role in sensing the chemical composition of the gastrointestinal content. The activity of this receptor may stimulate alpha gustducin, mediate PLC-beta-2 activation and lead to the gating of TRPM5
Gene Name:
TAS2R14
Uniprot ID:
Q9NYV8
Molecular weight:
36.0