ECHINACOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H46O20
Molecular Weight	786.7277
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCC3=CC=C(O)C(O)=C3)O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]2OC(=O)\C=C\C5=CC=C(O)C(O)=C5)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=FSBUXLDOLNLABB-ISAKITKMSA-N

InChI=1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19459316
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25077780 | https://www.ncbi.nlm.nih.gov/pubmed/27659301 | https://www.ncbi.nlm.nih.gov/pubmed/22805084

Echinacoside is a caffeic acid glycoside which is constituted from a trisaccharide consisting of two glucose and one rhamnose moieties glycosidically linked to one caffeic acid and on hydroxytyrosol residue at the centrally situated rhamnose. Echinacoside is the basic component of the roots of E. angustifolia and E. pallida, ranging from 0.5 to 1.0%. Echinacoside is reported to possess the immunostimulatory and high antioxidant activities

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
TGF beta Signaling Pathway 1 Target ID: WP1045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29033543	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Common cold 58 Sources: https://clinicaltrials.gov/ct2/show/NCT00065715	Primary	Phase III 665	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22805084	Primary	Basic research	Unknown Approved Use Unknown
Kidney fibrosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29033543	Primary	Basic research	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910 CYP19A1 429	P-gp 2052	P-gp 301 mCYP2E1 1 BCRP 101

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/885#sid=17389021	no [Activation 7.9433 uM]
BCRP 985	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144208143	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10969720/ \| https://pubchem.ncbi.nlm.nih.gov/bioassay/884#sid=17389021	unlikely [IC50 6290 uM]
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	yes
mCYP2E1 2	inducer 1966 Sources: http://jab.zsf.jcu.cz/pdfs/jab/2021/02/04.pdf	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29193364/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00G3AA	https://www.1pchem.com/search?query=1P00G3AA
A2B Chem	AH49954	http://a2bchem.com/prod/AH49954
AK Scientific	V1513	https://aksci.com/item_detail.php?cat=V1513
Ambeed	A125304	http://www.ambeed.com/search/Search.html?keyword=A125304
AstaTech	40412	http://astatechinc.com/CPSResult.php?CRNO=40412
Biopurify Phytochemicals	BP0520	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0520&searchhtmp=simplesearch&t=1
BioSynth	Q-100845	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100845
BLD Pharm	BD127126	http://www.bldpharm.com/search/Search.html?keyword=BD127126
BOC Sciences	82854-37-3	http://www.bocsci.com/description.asp?cas=82854-37-3
Chem Scene	CS-3400	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3400
Combi-Blocks	QV-0932	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-0932
eMolecules	17498026	https://orderbb.emolecules.com/search/#?query=17498026
eMolecules	206845168	https://orderbb.emolecules.com/search/#?query=206845168
eMolecules	95706716	https://orderbb.emolecules.com/search/#?query=95706716
KeyOrganics	AS-56376	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56376
mcule	MCULE-8160546274	https://mcule.com/MCULE-8160546274/
MedChem Express	HY-N0020	https://www.medchemexpress.com/search.html?q=HY-N0020&ft=&fa=&fp=
Molnova	M16077	https://www.molnova.com/en/serch-list.html?keywords=M16077
MolPort	MolPort-001-742-524	https://www.molport.com/shop/molecule-link/MolPort-001-742-524
TargetMol	BBP03838	https://www.targetmol.com/search?keyword=BBP03838
TargetMol	T1716	https://www.targetmol.com/search?keyword=T1716
Tetrahedron	TS75560	http://www.thsci.com/search.do?q=TS75560
W&J PharmaChem	50C567394	http://wjpharmachem.com/new/searcht.php?keyword=50C567394

PubMed

Title	Date	PubMed
Phenylpropanoid glycosides from plant cell cultures induce heme oxygenase 1 gene expression in a human keratinocyte cell line by affecting the balance of NRF2 and BACH1 transcription factors.	2012-08-30	22735309
Protective effects of echinacoside on carbon tetrachloride-induced hepatotoxicity in rats.	2007-03-22	17222497

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with Echinacoside at doses 20, 40 and 80 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

Rat pulmonary artery smooth muscle cells were incubated under normoxia, hypoxia, hypoxia + 0.35 mM echinacoside, or hypoxia + 0.4 mM echinacoside for 24 h. Cell viability was assessed by MTS assays.

Name

Type

Language

ECHINACOSIDE (ANG, PAL) (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]

Preferred Name

English

ECHINACOSIDE

Common Name

English

.BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->3)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->6))-, 4-(3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)

Systematic Name

English

ECHINACOSIDE [USP-RS]

Common Name

English

Code System Code Type Description

DRUG BANK

DB15488