Steviolbioside

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Steviolbioside are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Steviolbioside?

The molecule Steviolbioside presents a molecular formula of C32H50O13 and its IUPAC name is (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid.

Steviolbioside is a molecule found in the leaves of the plant Stevia rebaudiana. This molecule is responsible for the sweet taste of stevia. When steviolbioside is isolated and purified, it can be used as a natural sweetener..

Steviolbioside is about 300 times sweeter than sugar. However, it is not metabolized by the body and does not cause spikes in blood sugar levels. This makes steviolbioside a safe alternative to sugar for people with diabetes..

In addition to its sweetness, steviolbioside has been shown to have other health benefits. Studies have shown that steviolbioside can help lower blood pressure and improve cholesterol levels. It has also been shown to have anti-inflammatory and anti-cancer properties..

While steviolbioside is safe and has many health benefits, it is important to remember that it is still a sugar. Too much sugar, even natural sugar, can lead to weight gain and other health problems. Therefore, it is important to use steviolbioside in moderation..

3D structure

Cartesian coordinates

Geometry of Steviolbioside in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Steviolbioside OMHUCGDTACNQEX-OSHKXICASA-N chemical compound 2D structure molecule svg
Steviolbioside

 

Molecule descriptors

 
IUPAC name(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
InChI codeInChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(40)41)19(31)6-10-32(15,14-31)45-27-25(23(38)21(36)17(13-34)43-27)44-26-24(39)22(37)20(35)16(12-33)42-26/h16-27,33-39H,1,4-14H2,2-3H3,(H,40,41)/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1
InChI KeyOMHUCGDTACNQEX-OSHKXICASA-N
SMILESC=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C3

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Steviolbioside
  • (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
  • 07GV37SOFN
  • 13-[4,5-dihydroxy-6-(hydroxymethyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
  • 13alpha-[(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-5beta,8alpha,9beta,10alpha-kaur-16-en-18-oic acid
  • 41093-60-1
  • CCG-270321
  • CCRIS 6025
  • CCRIS-6025
  • CS-0022819
  • DB12434
  • HY-N2547
  • JC6
  • KAUR-16-EN-18-OIC ACID, 13-((2-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-, (4.ALPHA.)-
  • Kaur-16-en-18-oic acid, 13-((2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (4alpha)-
  • Q27236306
  • Steviobioside
  • Steviolbioside
  • XS167946
  • s9226

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • UNII-07GV37SOFN
  • AKOS037514896
  • CHEBI:145030

Physico-Chemical properties

IUPAC name(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
Molecular formulaC32H50O13
Molecular weight642.732
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity156.28
LogP-0.2
Topological polar surface area215.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.