ChemFOnt: Showing chemical card for Rebaudioside B (CFc000015966)

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

CFc000015966

Molecule Identification

Common Name

Rebaudioside B

Definition

Rebaudioside B, also known as stevioside A4, 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. Rebaudioside B, is found in minute quantities in stevia extracts, however, it is suspected that rebaudioside B is a byproduct of the isolation technique (doi:10.4141/P97-114). Rebaudioside B binds to the T1R2 and T1R3 (sweet) receptors as well as the T2R4 and T2R14 (bitter) receptors (PMID: 24705770 ). Rebaudioside B is not an endogenously occurring human metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rebaudioside B 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
Stevioside a4	HMDB
13-{[5-hydroxy-6-(hydroxymethyl)-3,4-bis({[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-carboxylate	Generator

Chemical Formula

C₃₈H₆₀O₁₈

Average Molecular Weight

804.8722

Monoisotopic Molecular Weight

804.377965116

IUPAC Name

13-{[5-hydroxy-6-(hydroxymethyl)-3,4-bis({[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 acid

Traditional Name

13-{[5-hydroxy-6-(hydroxymethyl)-3,4-bis({[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 acid

CAS Registry Number

58543-17-2

SMILES

CC12CCCC(C)(C1CCC13CC(=C)C(C1)(CCC23)OC1OC(CO)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1OC1OC(CO)C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(49)50)21(37)6-10-38(16,15-37)56-33-30(55-32-28(48)26(46)23(43)18(13-40)52-32)29(24(44)19(14-41)53-33)54-31-27(47)25(45)22(42)17(12-39)51-31/h17-33,39-48H,1,4-15H2,2-3H3,(H,49,50)

InChI Key

DRSKVOAJKLUMCL-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

Substituents

Steviol glycoside
Oligosaccharide
Diterpenoid
Kaurane diterpenoid
Fatty acyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

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: HMDB0034949)

Source

Endogenous

Endogenous (HMDB: HMDB0034949)

Animal

Animal (HMDB: HMDB0034949)

Exogenous

Food

Food (HMDB: HMDB0034949)

Exogenous (HMDB: HMDB0034949)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034949)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034949)

Lipid metabolism pathway (HMDB: HMDB0034949)

Cellular process

Cell signaling (HMDB: HMDB0034949)

Biochemical process

Lipid transport (HMDB: HMDB0034949)

Role

Biological role

Energy source (HMDB: HMDB0034949)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034949)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.28 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	294.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	186.13 m³·mol⁻¹	ChemAxon
Polarizability	83.21 Å³	ChemAxon
Number of Rings	7	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

HMDB0034949

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013542

KNApSAcK ID

Not Available

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

13370036

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Rebaudioside B (CFc000015966)

MOL for CFc000015966 (Rebaudioside B)

3D MOL for CFc000015966 (Rebaudioside B)

3D SDF for CFc000015966 (Rebaudioside B)

3D-SDF for CFc000015966 (Rebaudioside B)

PDB for CFc000015966 (Rebaudioside B)

3D PDB for CFc000015966 (Rebaudioside B)

SMILES for CFc000015966 (Rebaudioside B)

INCHI for CFc000015966 (Rebaudioside B)

Structure for CFc000015966 (Rebaudioside B)

3D Structure for CFc000015966 (Rebaudioside B)