ChemFOnt: Showing chemical card for Rebaudioside C (CFc000015964)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:05:20 UTC

Chemfont ID

CFc000015964

Molecule Identification

Common Name

Rebaudioside C

Definition

Rebaudioside C 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 C is one of the major sweetening constituents of commercial stevia accounting for up to 2% (by dry weight) of the stevia plant’s sweeteners (PMID: 19961353 ). Rebaudioside C binds to the T1R2 and T1R3 (sweet) receptors as well as the T2R4 and T2R14 (bitter) receptors (PMID: 24705770 ). Rebaudioside C is not an endogenously occurring human metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rebaudioside C 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Rebaudioside C	HMDB
Dulcoside b	HMDB
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 acid	Generator
Rebaudioside C	MeSH

Chemical Formula

C₄₄H₇₀O₂₂

Average Molecular Weight

951.0134

Monoisotopic Molecular Weight

950.435873924

IUPAC Name

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-carboxylate

Traditional Name

CAS Registry Number

63550-99-2

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 Key

QSRAJVGDWKFOGU-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034947)

Source

Endogenous

Endogenous (HMDB: HMDB0034947)

Animal

Animal (HMDB: HMDB0034947)

Exogenous

Food

Food (HMDB: HMDB0034947)

Exogenous (HMDB: HMDB0034947)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034947)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034947)

Lipid metabolism pathway (HMDB: HMDB0034947)

Cellular process

Cell signaling (HMDB: HMDB0034947)

Biochemical process

Lipid transport (HMDB: HMDB0034947)

Role

Biological role

Energy source (HMDB: HMDB0034947)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034947)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	353.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	217.02 m³·mol⁻¹	ChemAxon
Polarizability	98.43 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034947

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013540

KNApSAcK ID

C00037724

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13370040

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Rebaudioside C (CFc000015964)

MOL for CFc000015964 (Rebaudioside C)

3D MOL for CFc000015964 (Rebaudioside C)

3D SDF for CFc000015964 (Rebaudioside C)

3D-SDF for CFc000015964 (Rebaudioside C)

PDB for CFc000015964 (Rebaudioside C)

3D PDB for CFc000015964 (Rebaudioside C)

SMILES for CFc000015964 (Rebaudioside C)

INCHI for CFc000015964 (Rebaudioside C)

Structure for CFc000015964 (Rebaudioside C)

3D Structure for CFc000015964 (Rebaudioside C)