U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O3
Molecular Weight 318.4504
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STEVIOL

SMILES

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

InChI

InChIKey=QFVOYBUQQBFCRH-VQSWZGCSSA-N
InChI=1S/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,17+,18+,19+,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H30O3
Molecular Weight 318.4504
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Stevioside, an abundant component of Stevia rebaudiana leaf, has become well-known for its intense sweetness (250-300 times sweeter than sucrose) and is used as a non-caloric sweetener in several countries. Steviol and isosteviol (metabolic components of stevioside) may offer therapeutic benefits, as they have anti-hyperglycemic, anti-hypertensive, anti-inflammatory, anti-tumor, anti-diarrheal, diuretic, and immunomodulatory actions. In the presence of 16.7 mM glucose both stevioside and steviol enhance insulin secretion from incubated islets in a dose-dependent manner (1 nM to 1 mM). Even though both stevioside and steviol possess an insulinotropic/anti-hyperglycemic effect, steviol is more potent than stevioside. Steviol is an inhibitor of hOAT1 and hOAT3 organic anion transporters. Human organic anion transporter hOAT1 belongs to a superfamily of organic anion transporters, which play critical roles in the body disposition of clinically important drugs including anti-HIV therapeutics, anti-tumor drugs, antibiotics, anti-hypertensives, and anti-inflammatories. Highly purified steviol glycosides have repeatedly received Generally Recognized As Safe (GRAS) status from the US Food and Drug Administration in the past (FDA).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Mice: Experimental mice daily received steviol at doses of 40 and 200 mg/kg BW (10% of DMSO plus 90% of 0.9% normal saline) through an intraperitoneal (i.p.) injection.
Route of Administration: Intraperitoneal
A statistically significant activation of PXR- and AHR-responsive constructs was found after treatment with steviol at the concentration of 30 uM. Steviol dose-dependently activated AHR in HepG2 cells transfected with pXRE-luc, with EC50 equal to 7.5 uM. In human intestinal CACO2 cells, steviol and stevioside (at 10 uM concentration, 48-hour treatment) upregulated expression of both CYP1A2 and CYP1B1 genes at mRNA level.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:25:38 GMT 2023
Edited
by admin
on Fri Dec 15 19:25:38 GMT 2023
Record UNII
4741LYX6RT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STEVIOL
MI  
Common Name English
STEVIOL [MI]
Common Name English
(-)-STEVIOL
Common Name English
13-HYDROXYKAURENOIC ACID
Common Name English
(4.ALPHA.)-13-HYDROXYKAUR-16-EN-18-OIC ACID
Common Name English
KAUR-16-EN-18-OIC ACID, 13-HYDROXY-
Common Name English
HYDROXYDEHYDROSTEVIC ACID
Common Name English
STEVIOSIDE AGLYCON
Common Name English
NSC-226902
Code English
ENT-13-HYDROXY-KAURAN-16-EN-19-OIC ACID
Common Name English
REBAUDIOSIDES AGLYCON
Common Name English
KAUR-16-EN-18-OIC ACID, 13-HYDROXY-, (4.ALPHA.)-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50897427
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
CAS
471-80-7
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
CHEBI
145011
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
RXCUI
1363645
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m10208
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
STEVIOL
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
PUBCHEM
452967
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
CHEBI
145024
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
MESH
C012042
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
NSC
226902
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
DAILYMED
4741LYX6RT
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY
FDA UNII
4741LYX6RT
Created by admin on Fri Dec 15 19:25:38 GMT 2023 , Edited by admin on Fri Dec 15 19:25:38 GMT 2023
PRIMARY