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(O)=C(O)C=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(O)=C(O)C=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

Molecular Formula	C35H46O20
Molecular Weight	786.7277
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	1
Optical Activity	UNSPECIFIED

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 8297

Conditions

Condition	Modality	Highest Phase	Product
Common cold 58 Sources: https://clinicaltrials.gov/ct2/show/NCT00065715	Primary	Phase III 656	Unknown Approved Use Unknown
Parkinson's disease 226 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
inhibitor 1587 activator 80

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 BCRP 699 CYP19A1 60	P-gp 1537	P-gp 257 mCYP2E1 1 BCRP 75

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/884#sid=17389021	inconclusive [IC50 7.9433 uM]
CYP3A4 1925	activator 214 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/885#sid=17389021	no [Activation 7.9433 uM]
BCRP 773	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144208143	no
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10969720/	unlikely [IC50 6290 uM]
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/33730506/	yes
mCYP2E1 2	inducer 1573 Sources: http://jab.zsf.jcu.cz/pdfs/jab/2021/02/04.pdf	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 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
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
BioSynth	Q-100845	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100845
Biopurify Phytochemicals	BP0520	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0520&searchhtmp=simplesearch&t=1
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
KeyOrganics	AS-56376	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56376
MedChem Express	HY-N0020	https://www.medchemexpress.com/search.html?q=HY-N0020&ft=&fa=&fp=
MolPort	MolPort-001-742-524	https://www.molport.com/shop/molecule-link/MolPort-001-742-524
Molnova	M16077	https://www.molnova.com/en/serch-list.html?keywords=M16077
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
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
mcule	MCULE-8160546274	https://mcule.com/MCULE-8160546274/

PubMed

Title	Date	PubMed

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:32:11 UTC 2023` Edited by `admin` on `Sat Dec 16 08:32:11 UTC 2023`
Record UNII	I04O1DT48T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Common Name

English

ECHINACOSIDE [USP-RS]

Common Name

English

Code System Code Type Description

DRUG BANK

DB15488