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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

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

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

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

Description
Curator's Comment: description was created based on several sources, including: https://examine.com/supplements/stevia/ | https://www.ncbi.nlm.nih.gov/pubmed/15935396 | https://www.ncbi.nlm.nih.gov/pubmed/26712732

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

Sources: DOI: 10.1021/jo01125a012

Approval Year

Targets

Targets

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

Cmax

ValueDoseCo-administeredAnalytePopulation
4.24 μg/mL
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOSTEVIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1046.2 μg × min/mL
4 mg/kg single, intravenous
dose: 4 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ISOSTEVIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
632.3 μg × min/mL
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOSTEVIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
150.6 min
4 mg/kg single, intravenous
dose: 4 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ISOSTEVIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
169.9 min
4 mg/kg single, oral
dose: 4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ISOSTEVIOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

20 mg/kg of body weight
Route of Administration: Oral
Isosteviol prevented the growth of human cancer cells, with LD50 values of 84-167 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:45:58 GMT 2023
Edited
by admin
on Fri Dec 15 17:45:58 GMT 2023
Record UNII
091QB7QO95
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOSTEVIOL
Common Name English
NSC-231875
Code English
ISO-STEVIOL
Common Name English
(-)-ISOSTEVIOL
Common Name English
KETOISOSTEVIC ACID
Common Name English
17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4.ALPHA.,8.BETA.,13.BETA.)-
Common Name English
Code System Code Type Description
FDA UNII
091QB7QO95
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
NSC
231875
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID70950664
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
MESH
C515747
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
CAS
27975-19-5
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
PUBCHEM
99514
Created by admin on Fri Dec 15 17:45:58 GMT 2023 , Edited by admin on Fri Dec 15 17:45:58 GMT 2023
PRIMARY
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