Echinacoside

Identification

Summary

Echinacoside is a phenylethanoid glycoside plant isolate currently being investigated for anti-apoptotic and neuroprotective effects.

Generic Name
Echinacoside
DrugBank Accession Number
DB15488
Background

Echinacoside is a phenylethanoid glycoside isolated from Echinacea angustifolia in 1950, and currently being investigated for the treatment of Parkinson's, Alzheimer's, atherosclerosis, osteoporosis, acute colitis, wound treatment, and hepatitis.1 Echinacoside has demonstrated inhibition of apoptosis in neural cell lines, demonstrating potential for use in the treatment of neurological conditions.2

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 786.733
Monoisotopic: 786.258243881
Chemical Formula
C35H46O20
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

The neuroprotective effects are thought to be mediated via effects on mitogen-activated protein kinase, nuclear factor kappa-B, caspases 3 and 8, as well as CHOP pathways.1

TargetActionsOrganism
UGrowth hormone secretagogue receptor type 1
agonist
Humans
UAndrogen receptor
agonist
Humans
Absorption

Animal studies suggest an oral bioavailability of 0.83%.1

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

The metabolism of echinacoside has been investigated in rats and is thought to involve catechol O-methyltransferase as well as unspecified UDP-gluc- uronosyltransferases and sulfotransferases.3 A study of echinacoside's metabolism by human intestinal flora identified 13 metabolites which are produced independantly of human metabolism.4

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
EntacaponeThe metabolism of Echinacoside can be decreased when combined with Entacapone.
OpicaponeThe metabolism of Echinacoside can be decreased when combined with Opicapone.
Testosterone propionateThe metabolism of Echinacoside can be decreased when combined with Testosterone propionate.
TolcaponeThe metabolism of Echinacoside can be decreased when combined with Tolcapone.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
I04O1DT48T
CAS number
82854-37-3
InChI Key
FSBUXLDOLNLABB-ISAKITKMSA-N
InChI
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
IUPAC Name
(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
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]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

References

General References
  1. Liu J, Yang L, Dong Y, Zhang B, Ma X: Echinacoside, an Inestimable Natural Product in Treatment of Neurological and other Disorders. Molecules. 2018 May 18;23(5). pii: molecules23051213. doi: 10.3390/molecules23051213. [Article]
  2. Deng M, Zhao JY, Tu PF, Jiang Y, Li ZB, Wang YH: Echinacoside rescues the SHSY5Y neuronal cells from TNFalpha-induced apoptosis. Eur J Pharmacol. 2004 Nov 28;505(1-3):11-8. doi: 10.1016/j.ejphar.2004.09.059. [Article]
  3. Jia C, Shi H, Jin W, Zhang K, Jiang Y, Zhao M, Tu P: Metabolism of echinacoside, a good antioxidant, in rats: isolation and identification of its biliary metabolites. Drug Metab Dispos. 2009 Feb;37(2):431-8. doi: 10.1124/dmd.108.023697. Epub 2008 Nov 20. [Article]
  4. Li Y, Zhou G, Xing S, Tu P, Li X: Identification of Echinacoside Metabolites Produced by Human Intestinal Bacteria Using Ultraperformance Liquid Chromatography-Quadrupole Time-of-Flight Mass Spectrometry. J Agric Food Chem. 2015 Aug 5;63(30):6764-71. doi: 10.1021/acs.jafc.5b02881. Epub 2015 Jul 24. [Article]
  5. Zhou J, Zeng P, Sun JB, Wang FQ, Zhang Q: Application of two-phase hollow fiber liquid phase microextraction coupled with high-performance liquid chromatography for the study of the echinacoside pharmacokinetics in Parkinson's disease rat plasma. J Pharm Biomed Anal. 2013 Jul-Aug;81-82:27-33. doi: 10.1016/j.jpba.2013.03.020. Epub 2013 Apr 3. [Article]
KEGG Compound
C10450
ChemSpider
4445084
ChEBI
4745
ChEMBL
CHEMBL510539
ZINC
ZINC000085504689
Wikipedia
Echinacoside

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-1.364Zhou et al, 2013
Predicted Properties
PropertyValueSource
Water Solubility3.6 mg/mLALOGPS
logP0.14ALOGPS
logP-0.95ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area324.44 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity180.82 m3·mol-1ChemAxon
Polarizability77.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Peptide hormone binding
Specific Function
Receptor for ghrelin, coupled to G-alpha-11 proteins. Stimulates growth hormone secretion. Binds also other growth hormone releasing peptides (GHRP) (e.g. Met-enkephalin and GHRP-6) as well as non-...
Gene Name
GHSR
Uniprot ID
Q92847
Uniprot Name
Growth hormone secretagogue receptor type 1
Molecular Weight
41328.045 Da
References
  1. Wu CJ, Chien MY, Lin NH, Lin YC, Chen WY, Chen CH, Tzen JTC: Echinacoside Isolated from Cistanche tubulosa Putatively Stimulates Growth Hormone Secretion via Activation of the Ghrelin Receptor. Molecules. 2019 Feb 17;24(4). pii: molecules24040720. doi: 10.3390/molecules24040720. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Jiang Z, Zhou B, Li X, Kirby GM, Zhang X: Echinacoside Increases Sperm Quantity in Rats by Targeting the Hypothalamic Androgen Receptor. Sci Rep. 2018 Mar 1;8(1):3839. doi: 10.1038/s41598-018-22211-1. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Jia C, Shi H, Jin W, Zhang K, Jiang Y, Zhao M, Tu P: Metabolism of echinacoside, a good antioxidant, in rats: isolation and identification of its biliary metabolites. Drug Metab Dispos. 2009 Feb;37(2):431-8. doi: 10.1124/dmd.108.023697. Epub 2008 Nov 20. [Article]

Drug created on September 04, 2019 14:47 / Updated on June 12, 2020 16:53