Epimedin I

Details

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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

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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

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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

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2D Structure of Epimedin I

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Epimedium koreanum

Cross-Links

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PubChem 5318835
NPASS NPC299282