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Details

Stereochemistry ABSOLUTE
Molecular Formula C36H56O9
Molecular Weight 632.8244
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALENDULOSIDE E

SMILES

[H][C@@]6(O[C@H]1CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]5(CC[C@@]34C)C(O)=O)C1(C)C)O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O

InChI

InChIKey=IUCHKMAZAWJNBJ-RCYXVVTDSA-N
InChI=1S/C36H56O9/c1-31(2)14-16-36(30(42)43)17-15-34(6)19(20(36)18-31)8-9-22-33(5)12-11-23(32(3,4)21(33)10-13-35(22,34)7)44-29-26(39)24(37)25(38)27(45-29)28(40)41/h8,20-27,29,37-39H,9-18H2,1-7H3,(H,40,41)(H,42,43)/t20-,21-,22+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22807953 | http://www.hmdb.ca/metabolites/HMDB40851

Calenduloside E (3-O-[beta-d-glucuronopyranosyl]oleanolic acid), the glucuronic acid conjugate of oleanolic acid, is a triterpenoid saponin present in a wide variety of Aralia plants, in which the content of calenduloside E is about 0.02%. A number of studies of the biological activity of calenduloside E has been reported since its first isolation by Kasprzyk and Wojciechowski. These studies indicate that calenduloside E has hypoglycemic activity and is potentially useful in the treatment of diabetes and morbid obesity. It may also be useful as a spermicidal contraceptive and as an antiarrhythmic agent. Because of its wide-ranging biological activity and low toxicity, the potential clinical use of calenduloside E has attracted much attention in recent years. Furthermore, its active metabolite, oleanolic acid, has been shown to possess analgesic, antiinflammatory, hepatoprotective, antitumor and hypolipidemic effects as well as having hypoglycemic activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Calenduloside E 6'-methyl ester induces apoptosis in CT-26 mouse colon carcinoma cells and inhibits tumor growth in a CT-26 xenograft animal model.
2012 Jul
Pharmacokinetic study of calenduloside E and its active metabolite oleanolic acid in beagle dog using liquid chromatography-tandem mass spectrometry.
2014 Mar 1
Patents

Patents

Sample Use Guides

In pharmacokinetic study Calenduloside E was administered as single oral and intravenous doses to dogs. The oral dose was formulated in a capsule with -cyclodextrin as excipient and administered at doses of 1.05, 2.10 and 4.20 mg/kg. The intravenous dose was formulated at a concentration of 5 mg/mL in a vehicle of polyethylene glycol 400:saline (2:1, v/v) and administered at a dose of 2.10 mg/kg.
Route of Administration: Other
The spermicidal activity of OAG was assayed according to the Sander–Cramer method. Varying concentrations of OAG solution were prepared in physiological saline (0, 10, 30, 40, 50, 60 mkg/mL) and 100 mkL of each was mixed with an aliquot of 20 mkL of sperm suspension. The specimens were examined under a phase contrast microscope (×100) after 20 s of treatment and counted for motile sperm.
Name Type Language
CALENDULOSIDE E
Common Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.)-17-CARBOXY-28-NOROLEAN-12-EN-3-YL
Common Name English
OLEANOLIC ACID 3-O-GLUCURONIDE
Common Name English
3-O-(.BETA.-D-GLUCOPYRANURONOSYL)OLEANOLIC ACID
Common Name English
OLEAN-12-EN-28-OIC ACID, 3.BETA.-(.BETA.-D-GLUCOPYRANURONOSYLOXY)-
Common Name English
MOMORDIN IB
Common Name English
GLUCOPYRANOSIDURONIC ACID, 3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID, .BETA.-D-
Common Name English
OLEANOLIC ACID 3-O-.BETA.-D-GLUCURONOPYRANOSIDE
Common Name English
POLYSCIASAPONIN P7
Common Name English
28-DESGLUCOSYLCHIKUSETSUSAPONIN IVA
Common Name English
GLYCOSIDE ST-E
Common Name English
SILPHIOSIDE F
Common Name English
Code System Code Type Description
DAILYMED
184358RYCU
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY
RXCUI
1428039
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID90180668
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY
PUBCHEM
176079
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY
CAS
26020-14-4
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY
CHEBI
37658
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY
FDA UNII
184358RYCU
Created by admin on Fri Dec 15 21:50:30 GMT 2023 , Edited by admin on Fri Dec 15 21:50:30 GMT 2023
PRIMARY