RUBUSOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H50O13
Molecular Weight	642.7316
Optical Activity	UNSPECIFIED
Defined Stereocenters	16 / 16
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@]3(C[C@]1(CC3=C)CC[C@]4([H])[C@@](C)(CCC[C@@]24C)C(=O)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O

InChI

InChIKey=YWPVROCHNBYFTP-OSHKXICASA-N

InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(41)44-26-24(39)22(37)20(35)16(12-33)42-26)19(31)6-10-32(15,14-31)45-27-25(40)23(38)21(36)17(13-34)43-27/h16-27,33-40H,1,4-14H2,2-3H3/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C32H50O13
Molecular Weight	642.7316
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	16 / 16
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26198882 | https://www.ncbi.nlm.nih.gov/pubmed/28410552 | https://www.ncbi.nlm.nih.gov/pubmed/26306809 | https://www.ncbi.nlm.nih.gov/pubmed/25152415

Rubusoside is a natural sweetener and a solubilizing agent with antiangiogenic and antiallergic properties. Rubusoside (Rub) is a natural sweetener from the Chinese sweet tea plant (Rubus suavissimus) and closely related to glucosides found in stevia leaf (Stevia rebaudiana). Teas made from the leaves of Rubus suavissimus have been shown to be associated with caloric restriction to aid in the weight loss by obese individuals. Rubusoside is an excellent solubilizing agent. It can enhance the solubility of a number of pharmaceutically important compounds, such as liquiritin, teniposide, curcumin, and etoposide. Rubusoside inhibits hexose transport by GLUT5 and GLUT1.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucose transporter 1 Target ID: CHEMBL2535 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26306809	Inhibitor 8297		6.7 mM [IC50]
Solute carrier family 2, facilitated glucose transporter member 5 1 Target ID: CHEMBL5875 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26306809	Inhibitor 8297		4.6 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27648352	Primary		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28410552	Inactive ingredient		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Production of rubusoside from stevioside by using a thermostable lactase from Thermus thermophilus and solubility enhancement of liquiritin and teniposide.	2014 Oct	25152415
Inhibition of human GLUT1 and GLUT5 by plant carbohydrate products; insights into transport specificity.	2015 Aug 26	26306809
Cariogenicity features of Streptococcus mutans in presence of rubusoside.	2016 May 11	27169524
Employing rubusoside to improve the solubility and permeability of antitumor compound betulonic acid.	2016 Nov	27759492

Patents

Sample Use Guides

In Vivo Use Guide

Mice: In an in vivo efficacy study, the tumor growth in the S180 berry mice orally dosed with BEA-NP at 75 mg/kg was inhibited by 50%.

Route of Administration: Oral

In Vitro Use Guide

Rubusoside (Rub) inhibits human GLUT1 and GLUT5 with an IC50 of 4.6± 0.3mM and 6.7± 0.2mM, respectively. 20mM Rub reduced GLUT5 activity to less than 5% of maximum levels.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:42:10 UTC 2023` Edited by `admin` on `Sat Dec 16 01:42:10 UTC 2023`
Record UNII	TCV5K3M3GX
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RUBUSOSIDE

Official Name

English

KAUR-16-EN-18-OIC ACID, 13-(.BETA.-D-GLUCOPYRANOSYLOXY)-, .BETA.-D-GLUCOPYRANOSYL ESTER, (4.ALPHA.)-

Common Name

English

RUB

Common Name

English

RUBUSOSIDE [INCI]

Common Name

English

Code System Code Type Description

MESH

C056177