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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:52:45 UTC
Update Date2021-09-14 15:18:04 UTC
HMDB IDHMDB0034947
Secondary Accession Numbers
  • HMDB34947
Metabolite Identification
Common NameRebaudioside C
DescriptionRebaudioside C, also known as dulcoside b, 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 C is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862640
Synonyms
ValueSource
(-)-Rebaudioside CHMDB
Dulcoside bHMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[5-hydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acidGenerator
Rebaudioside CMeSH
Chemical FormulaC44H70O22
Average Molecular Weight951.0134
Monoisotopic Molecular Weight950.435873924
IUPAC Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[5-hydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate
Traditional Name3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 13-{[5-hydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate
CAS Registry Number63550-99-2
SMILES
CC1OC(OC2C(OC34CC5(CC3=C)CCC3C(C)(CCCC3(C)C(=O)OC3OC(CO)C(O)C(O)C3O)C5CC4)OC(CO)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C44H70O22/c1-17-12-43-10-6-22-41(3,8-5-9-42(22,4)40(58)65-38-33(57)30(54)26(50)20(14-46)61-38)23(43)7-11-44(17,16-43)66-39-35(64-36-31(55)28(52)24(48)18(2)59-36)34(27(51)21(15-47)62-39)63-37-32(56)29(53)25(49)19(13-45)60-37/h18-39,45-57H,1,5-16H2,2-4H3
InChI KeyQSRAJVGDWKFOGU-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentSteviol glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP10(-1.1) g/LALOGPS
logP10(-2.9) g/LChemAxon
logS10(-1.9) g/LALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area353.9 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity217.02 m³·mol⁻¹ChemAxon
Polarizability98.43 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 10V, Positive-QTOFsplash10-01zi-0302406903-fcd9c7639287ce3df0f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 20V, Positive-QTOFsplash10-01wf-0204509500-42eed6c676a3b4f4a49c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 40V, Positive-QTOFsplash10-00nf-0305209301-f3b1f957f4ad7277ce042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 10V, Negative-QTOFsplash10-02aa-1500305926-776564aeab0f77acb9b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 20V, Negative-QTOFsplash10-03di-1900304423-40ebddf134efb1065d982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 40V, Negative-QTOFsplash10-01t9-4901303010-a5f6e05efeaf58381ba82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 10V, Positive-QTOFsplash10-0uki-0001402908-4e7cefd45e570b3df05f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 20V, Positive-QTOFsplash10-0udi-1308304419-c6574750f9d411a2c0262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 40V, Positive-QTOFsplash10-05g3-9103000341-5ccb30df3f6eed74b2192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 10V, Negative-QTOFsplash10-0002-0100000329-5ff3e69cee0d3105aee82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 20V, Negative-QTOFsplash10-000i-5100000393-6b1631b1b83d97a7567f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rebaudioside C 40V, Negative-QTOFsplash10-009l-5000009320-8a9cb29443c3cd957d522021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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 IDFDB013540
KNApSAcK IDC00037724
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13370040
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.