Epimedoside A

Details

• Internal ID: f355f169-00b0-438d-99f2-96051767bbad
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C32H38O15/c1-12(2)4-9-16-18(44-32-27(42)25(40)22(37)19(11-33)45-32)10-17(35)20-23(38)30(47-31-26(41)24(39)21(36)13(3)43-31)28(46-29(16)20)14-5-7-15(34)8-6-14/h4-8,10,13,19,21-22,24-27,31-37,39-42H,9,11H2,1-3H3/t13-,19+,21-,22+,24+,25-,26+,27+,31-,32+/m0/s1
• InChI Key: OGYXOOJUJQIDOX-FVCAYHPDSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₅
• Molecular Weight: 662.60 g/mol
• Exact Mass: 662.22107050 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 39012-04-9
• 5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• Epimedoside-A
• C32H38O15
• DTXSID90192286
• HY-N2626
• AKOS032961872
• MS-31024
• CS-0023034
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8664	86.64%
Caco-2	-	0.9340	93.40%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7171	71.71%
OATP2B1 inhibitior	-	0.7102	71.02%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8694	86.94%
P-glycoprotein inhibitior	+	0.5959	59.59%
P-glycoprotein substrate	-	0.5402	54.02%
CYP3A4 substrate	+	0.6409	64.09%
CYP2C9 substrate	-	0.6532	65.32%
CYP2D6 substrate	-	0.8528	85.28%
CYP3A4 inhibition	-	0.9436	94.36%
CYP2C9 inhibition	-	0.7241	72.41%
CYP2C19 inhibition	-	0.6819	68.19%
CYP2D6 inhibition	-	0.8386	83.86%
CYP1A2 inhibition	-	0.6373	63.73%
CYP2C8 inhibition	+	0.7276	72.76%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7420	74.20%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.5028	50.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6611	66.11%
Micronuclear	-	0.5367	53.67%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8659	86.59%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6706	67.06%
Acute Oral Toxicity (c)	III	0.6098	60.98%
Estrogen receptor binding	+	0.7931	79.31%
Androgen receptor binding	+	0.6508	65.08%
Thyroid receptor binding	-	0.4949	49.49%
Glucocorticoid receptor binding	+	0.6190	61.90%
Aromatase binding	+	0.5742	57.42%
PPAR gamma	+	0.7035	70.35%
Honey bee toxicity	-	0.6947	69.47%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9827	98.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.68%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.89%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	95.12%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.30%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.96%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.37%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	91.78%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.61%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.53%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.59%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.01%	91.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.88%	95.64%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.44%	93.10%
CHEMBL3194	P02766	Transthyretin	83.38%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.62%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.53%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.01%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.96%	94.75%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium acuminatum
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Stipa robusta
• Succisa pratensis
• Vancouveria hexandra

Cross-Links

• PubChem: 5317093
• NPASS: NPC145858
• LOTUS: LTS0171943
• wikiData: Q72470872