PhytoHub: Showing entry for Rebaudioside A

Rebaudioside A

Identification

PhytoHub ID

PHUB002066

Name

Rebaudioside A

Systematic Name

Not Available

Synonyms

Rebaudiana a
Stevioside A3
Truvia

CAS Number

Not Available

Average Mass

967.021

Monoisotopic Mass

966.430788514

Chemical Formula

C₄₄H₇₀O₂₃

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,5R,9S,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

InChI Key

HELXLJCILKEWJH-UXNRVLLZSA-N

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

SMILES

C[C@@]12CCC[C@](C)(C1CC[C@@]13CC(=C)[C@@](C1)(CCC23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.44e+01 g/l
LogS (ALOGPS): -1.83
LogP (ALOGPS): -1.45
Hydrogen Acceptors: 22
Hydrogen Donors: 14
Rotatable Bond Count: 13
Polar Surface Area: 374.13000000000005
Refractivity: 218.56279999999987
Polarizability: 98.21419080244738
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -3.648397751535034
pKa (strongest acidic): 11.750304583017469
Number of Rings: 8
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: Yes

External Links

PubChem: 6918840
HMDB: HMDB34950
KNApSAcK: C00023175
FooDB (Compounds): FDB013543

Taxonomy as Food Phytochemical

Family: Terpenoids
Class: Diterpenoids
Sub-class: Not Available

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Prenol lipids
Super-class: Lipids and lipid-like molecules
Sub-class: Terpene glycosides
Direct Parent Name: Steviol glycosides
Alternative Parent Names: ["Acetals", "Carbonyl compounds", "Carboxylic acid esters", "Fatty acyl glycosides", "Hydrocarbon derivatives", "Kaurane diterpenoids", "Monocarboxylic acids and derivatives", "O-glycosyl compounds", "Oligosaccharides", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Polyols", "Primary alcohols", "Secondary alcohols"]
External Descriptor Annotations: Not Available
Substituent Names: ["Acetal", "Alcohol", "Aliphatic heteropolycyclic compound", "Carbonyl group", "Carboxylic acid derivative", "Carboxylic acid ester", "Diterpenoid", "Fatty acyl", "Fatty acyl glycoside", "Glycosyl compound", "Hydrocarbon derivative", "Kaurane diterpenoid", "Monocarboxylic acid or derivatives", "O-glycosyl compound", "Oligosaccharide", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Polyol", "Primary alcohol", "Secondary alcohol", "Steviol glycoside"]

Spectra from Phytohub

	Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Food Sources

	Name	Group
	Stevia (Stevia rebaudiana)	Vegetables, Leaf vegetables	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Rebaudioside A		Steviol	human	plasma	gut microbiota metabolite	Not Available	0.5-2µmol/L	Not Available	C₂₀H₃₀O₃	318.219494826	Detailed Intervention Studies	Publications
	Rebaudioside A		Steviol glucuronide	human	plasma	host-gut microbiota co-metabolite	12h-24h	<20 nmol/L	Not Available	C₂₆H₃₈O₉	494.251582804	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Rebaudioside A