Showing Compound Card for Rebaudioside A (CDB005049)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-17 19:04:10 UTC
Updated at2020-12-07 19:11:29 UTC
CannabisDB IDCDB005049
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameRebaudioside A
Descriptionrebaudioside A, also known as reb a or stevia, 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. rebaudioside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Rebaudioside A is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight967.02
Monoisotopic Molecular Weight966.4308
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point242 - 244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-0uxr-0000000079-75402eef616f2b12831c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-0udi-0000000090-fb46c72609f54077cf9f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 60V, negativesplash10-0udl-0001206090-44ebe132417d2ec16d002020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 80V, negativesplash10-00or-0004903000-5f4f5ef5cb14a46c04042020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0003407944-099a80a1866d9d12a98a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0016-0105609510-c96697836b2d1aafe2ca2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0114219321-3f7bdf66df4e62b9d7352016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ftk-0301406869-401b87bfebcf28e217d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01tj-0810517978-553fcbc8360b4f9758782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2912405030-6a11a761d8d227a3bcf92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0000001269-f47808f99d3ef6acf1002021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8300001397-f498c720bf4e6a9aacd12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-5100009231-030e605dab68d0397f942021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-0101608955-231c87c74fb5ee2e0ca32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ktf-2627409455-184dd1d1d8afaa68067f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9803304652-6890556b9fa860d144f52021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034950
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available