Echinacoside

Details

• Internal ID: 1d5ff21f-92dc-4aee-9df1-13b73b68303d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• 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]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• 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
• InChI Key: FSBUXLDOLNLABB-ISAKITKMSA-N
• Popularity: 172 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₂₀
• Molecular Weight: 786.70 g/mol
• Exact Mass: 786.25824385 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -3.19
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

• 82854-37-3
• UNII-I04O1DT48T
• CHEBI:4745
• I04O1DT48T
• [(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]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• DTXSID0033469
• 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), beta-D-
• AC1NQZ1Q
• Echinacoside,(S)
• MFCD00075695
• SureCN525502
• DSSTox_CID_13469
• ECHINACOSIDE [USP-RS]
• Echinacoside, 98% (HPLC)
• SCHEMBL525502
• CHEMBL510539
• MEGxp0_001773
• DTXCID8013469
• Echinacoside, analytical standard
• HMS3885K04
• HY-N0020
• Tox21_200945
• C35H40O20
• s3783
• AKOS015897141
• CCG-270479
• CS-3400
• DB15488
• C35-H40-O20
• NCGC00091915-01
• NCGC00091915-02
• NCGC00258498-01
• AC-34699
• AS-56376
• LS-71510
• CAS-82854-37-3
• A12039
• Q475631
• Echinacoside, primary pharmaceutical reference standard
• Echinacoside, United States Pharmacopeia (USP) Reference Standard
• (2R,3R,4R,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-5-hydroxy-2-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl 3-(3,4-dihydroxyphenyl)acrylate
• .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)
• [(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)tetrahydropyran-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 2-(3,4-dihydroxyphenyl)ethyl 6-deoxy-alpha-L-mannopyranosyl-(1-3)-[beta-D-glucopyranosyl-(1-6)]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
• 3,4-Dihydroxyphenethyl 3-O-(alpha-L-rhamnopyranosyl)-4-O-(3,4-dihydroxycinnamoyl)-6-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside
• 737806-07-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7512	75.12%
Caco-2	-	0.9023	90.23%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8606	86.06%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8241	82.41%
P-glycoprotein inhibitior	-	0.4647	46.47%
P-glycoprotein substrate	-	0.5706	57.06%
CYP3A4 substrate	+	0.6614	66.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.7548	75.48%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.7078	70.78%
CYP inhibitory promiscuity	-	0.7002	70.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6737	67.37%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7265	72.65%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9491	94.91%
Acute Oral Toxicity (c)	III	0.7702	77.02%
Estrogen receptor binding	+	0.7963	79.63%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.5256	52.56%
Glucocorticoid receptor binding	+	0.5456	54.56%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7078	70.78%
Honey bee toxicity	-	0.6695	66.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7970	79.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	501.2 nM; 501.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	100 nM; 1995.3 nM; 100 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.65%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.56%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.87%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.77%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.48%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.50%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	93.21%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.89%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.70%	86.92%
CHEMBL3194	P02766	Transthyretin	92.66%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.11%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.21%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.83%	96.37%
CHEMBL226	P30542	Adenosine A1 receptor	83.74%	95.93%
CHEMBL4208	P20618	Proteasome component C5	83.43%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.98%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.87%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.26%	94.80%

Plants that contains it

• Buddleja globosa
• Buddleja officinalis
• Cistanche deserticola
• Cistanche mongolica
• Cistanche phelypaea
• Cistanche salsa
• Digitalis purpurea
• Echinacea angustifolia
• Echinacea atrorubens
• Echinacea pallida
• Echinacea paradoxa
• Jasminum mesnyi
• Ligustrum vulgare
• Magnolia sieboldii
• Marrubium velutinum
• Pedicularis plicata
• Pedicularis striata
• Penstemon crandallii
• Penstemon secundiflorus
• Phlomis brunneogaleata
• Plantago maritima
• Rehmannia glutinosa
• Rosa rugosa
• Syringa reticulata
• Verbascum wiedemannianum

Cross-Links

• PubChem: 5281771
• NPASS: NPC298257
• ChEMBL: CHEMBL510539
• LOTUS: LTS0002111
• wikiData: Q475631