Epimedin I

Details

• Internal ID: e39d94e5-c598-4234-b560-550d61d476aa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2S,3S,4S,5R,6S)-5-hydroxy-6-[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-2-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
• 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)OC)O)OC6C(C(C(C(O6)CO)O)O)O)OC(=O)C
• 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)OC)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC(=O)C
• InChI: InChI=1S/C41H52O21/c1-15(2)6-11-20-22(57-39-31(51)29(49)26(46)23(13-42)58-39)12-21(45)25-28(48)37(35(60-36(20)25)18-7-9-19(54-5)10-8-18)61-41-33(53)38(34(16(3)55-41)56-17(4)44)62-40-32(52)30(50)27(47)24(14-43)59-40/h6-10,12,16,23-24,26-27,29-34,38-43,45-47,49-53H,11,13-14H2,1-5H3/t16-,23+,24+,26+,27+,29-,30-,31+,32+,33+,34-,38-,39+,40-,41-/m0/s1
• InChI Key: DSBGQYHARXPXRK-XXJCEPRQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₅₂O₂₁
• Molecular Weight: 880.80 g/mol
• Exact Mass: 880.30010866 g/mol
• Topological Polar Surface Area (TPSA): 320.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -1.54
• H-Bond Acceptor: 21
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

• Epimedin I
• [(2S,3S,4S,5R,6S)-5-hydroxy-6-[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-2-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
• 205445-00-7
• HY-N8086
• AKOS040757219
• CS-0139926

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7770	77.70%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6111	61.11%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8546	85.46%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9459	94.59%
P-glycoprotein inhibitior	+	0.7049	70.49%
P-glycoprotein substrate	+	0.5719	57.19%
CYP3A4 substrate	+	0.6918	69.18%
CYP2C9 substrate	-	0.6377	63.77%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.9451	94.51%
CYP2C9 inhibition	-	0.7163	71.63%
CYP2C19 inhibition	-	0.7160	71.60%
CYP2D6 inhibition	-	0.8765	87.65%
CYP1A2 inhibition	-	0.8073	80.73%
CYP2C8 inhibition	+	0.6986	69.86%
CYP inhibitory promiscuity	-	0.7291	72.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7142	71.42%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9068	90.68%
Skin irritation	-	0.8163	81.63%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.5328	53.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7637	76.37%
Micronuclear	-	0.5067	50.67%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8596	85.96%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7434	74.34%
Acute Oral Toxicity (c)	III	0.6254	62.54%
Estrogen receptor binding	+	0.8042	80.42%
Androgen receptor binding	+	0.6841	68.41%
Thyroid receptor binding	+	0.5688	56.88%
Glucocorticoid receptor binding	+	0.6514	65.14%
Aromatase binding	+	0.5474	54.74%
PPAR gamma	+	0.7394	73.94%
Honey bee toxicity	-	0.6656	66.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9710	97.10%

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	99.86%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.49%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.59%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.72%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.65%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.90%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.85%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.06%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	91.66%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.45%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.15%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.03%	95.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.43%	81.11%
CHEMBL4208	P20618	Proteasome component C5	82.84%	90.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.70%	87.67%
CHEMBL340	P08684	Cytochrome P450 3A4	82.30%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.05%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.99%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.50%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.03%	94.42%

Plants that contains it

• Epimedium koreanum

Cross-Links

• PubChem: 5318835
• NPASS: NPC299282