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
Structure for Echinacoside (DB15488)
- Weight
- Average: 786.733
Monoisotopic: 786.258243881 - Chemical Formula
- C35H46O20
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism UGrowth hormone secretagogue receptor type 1 agonistHumans UAndrogen receptor agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareEntacapone The metabolism of Echinacoside can be decreased when combined with Entacapone. Opicapone The metabolism of Echinacoside can be decreased when combined with Opicapone. Testosterone propionate The metabolism of Echinacoside can be decreased when combined with Testosterone propionate. Tolcapone The metabolism of Echinacoside can be decreased when combined with Tolcapone. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- KEGG Compound
- C10450
- ChemSpider
- 4445084
- ChEBI
- 4745
- ChEMBL
- CHEMBL510539
- ZINC
- ZINC000085504689
- Wikipedia
- Echinacoside
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Recruiting Treatment Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -1.364 Zhou et al, 2013 - Predicted Properties
Property Value Source Water Solubility 3.6 mg/mL ALOGPS logP 0.14 ALOGPS logP -0.95 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 9.01 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 19 Chemaxon Hydrogen Donor Count 12 Chemaxon Polar Surface Area 324.44 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 180.82 m3·mol-1 Chemaxon Polarizability 77.02 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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
- 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
- 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 at September 04, 2019 14:47 / Updated at June 12, 2020 16:53