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Details

Stereochemistry ABSOLUTE
Molecular Formula C48H76O19
Molecular Weight 957.1056
Optical Activity UNSPECIFIED
Defined Stereocenters 23 / 23
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALENDULOSIDE H

SMILES

[H][C@@]8(O[C@H]1[C@H](O)[C@H](O[C@@]([H])(O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC=C5[C@]6([H])CC(C)(C)CC[C@@]6(CC[C@@]45C)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)C2(C)C)[C@@H]1O)C(O)=O)O[C@H](CO)[C@H](O)[C@H](O)[C@H]8O

InChI

InChIKey=QZMAEZWZCGBZFK-AOJWCAIYSA-N
InChI=1S/C48H76O19/c1-43(2)14-16-48(42(61)67-40-33(56)31(54)29(52)24(20-50)63-40)17-15-46(6)21(22(48)18-43)8-9-26-45(5)12-11-27(44(3,4)25(45)10-13-47(26,46)7)64-41-35(58)36(34(57)37(66-41)38(59)60)65-39-32(55)30(53)28(51)23(19-49)62-39/h8,22-37,39-41,49-58H,9-20H2,1-7H3,(H,59,60)/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31-,32+,33+,34-,35+,36-,37-,39-,40-,41+,45-,46+,47+,48-/m0/s1

HIDE SMILES / InChI

Molecular Formula C48H76O19
Molecular Weight 957.1056
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 23 / 23
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://link.springer.com/referenceworkentry/10.1007%2F978-1-4614-0541-2_70

CALENDULOSIDE H is the derivative of oleanolic acid present in a wide variety of Caltha plants. CALENDULOSIDE H exhibited marked antiinflammatory activity in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.
2006 Dec

Sample Use Guides

CALENDULOSIDE H exhibited marked antiinflammatory activity, with ID50 values of 0.20 mg per ear in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice.
Route of Administration: Topical
CALENDULOSIDE H exhibited marked antiinflammatory activity against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibition of EBV-EA activation was assayed using Raji cells (virus nonproducer), the EBV genome-carrying human lymphoblastoid cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:17:54 GMT 2023
Edited
by admin
on Fri Dec 15 20:17:54 GMT 2023
Record UNII
XRX4A17TSS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CALENDULOSIDE H
Common Name English
CALENDULAGLYCOSIDE C
Common Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.)-28-(.BETA.-D-GLUCOPYRANOSYLOXY)-28-OXOOLEAN-12-EN-3-YL 3-O-.BETA.-D-GALACTOPYRANOSYL-
Common Name English
Code System Code Type Description
CAS
26020-29-1
Created by admin on Fri Dec 15 20:17:54 GMT 2023 , Edited by admin on Fri Dec 15 20:17:54 GMT 2023
PRIMARY
FDA UNII
XRX4A17TSS
Created by admin on Fri Dec 15 20:17:54 GMT 2023 , Edited by admin on Fri Dec 15 20:17:54 GMT 2023
PRIMARY
PUBCHEM
44566500
Created by admin on Fri Dec 15 20:17:54 GMT 2023 , Edited by admin on Fri Dec 15 20:17:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID60180670
Created by admin on Fri Dec 15 20:17:54 GMT 2023 , Edited by admin on Fri Dec 15 20:17:54 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid