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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 ISOSTEVIOL

SMILES

C[C@]12C[C@@]3(CC1=O)CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(O)=O)[C@@H]3CC2

InChI

InChIKey=KFVUFODCZDRVSS-XGBBNYNSSA-N
InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1

HIDE SMILES / InChI

Description

Stevia is the common word to refer to the plant stevia rebaudiana which is the sweetest of the stevia species of plants and historically used as a sweetening agent. Several studies have suggested that in addition to their sweetness, steviosides and their related compounds, including rebaudioside A and isosteviol, may offer additional therapeutic benefits. These benefits include anti-hyperglycaemic, anti-hypertensive, anti-inflammatory, anti-tumor, anti-diarrheal, diuretic, and immunomodulatory actions. Isosteviol inhibits DNA polymerases and human DNA topoisomerase II. It also retards growth of three different types of human cancer cells and inhibits inflammation induced by TPA. Isosteviol had been in phase II clinical trials for the treatment of Type 2 diabetes mellitus.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
27.5 µM [Ki]
103.0 µM [IC50]
177.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
4.24 μg/mL
4 mg/kg single, oral
ISOSTEVIOL plasma
Rattus norvegicus

AUC

ValueDoseCo-administeredAnalytePopulation
1046.2 μg × min/mL
4 mg/kg single, intravenous
ISOSTEVIOL plasma
Rattus norvegicus
632.3 μg × min/mL
4 mg/kg single, oral
ISOSTEVIOL plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
150.6 min
4 mg/kg single, intravenous
ISOSTEVIOL plasma
Rattus norvegicus
169.9 min
4 mg/kg single, oral
ISOSTEVIOL plasma
Rattus norvegicus

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
20 mg/kg of body weight
Route of Administration: Oral
In Vitro Use Guide
Isosteviol prevented the growth of human cancer cells, with LD50 values of 84-167 uM.