Epimedin C

Details

• Internal ID: b4d64221-afb9-4c32-9a99-d74be83234d0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=C(C3=O)C(=CC(=C4CC=C(C)C)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC=C(C=C6)OC)C)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]([C@@H](O[C@H]2OC3=C(OC4=C(C3=O)C(=CC(=C4CC=C(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C6=CC=C(C=C6)OC)C)O)O)O)O)O
• InChI: InChI=1S/C39H50O19/c1-14(2)6-11-19-21(54-38-32(50)29(47)26(44)22(13-40)55-38)12-20(41)23-27(45)35(33(56-34(19)23)17-7-9-18(51-5)10-8-17)57-39-36(30(48)25(43)16(4)53-39)58-37-31(49)28(46)24(42)15(3)52-37/h6-10,12,15-16,22,24-26,28-32,36-44,46-50H,11,13H2,1-5H3/t15-,16-,22+,24-,25-,26+,28+,29-,30+,31+,32+,36+,37-,38+,39-/m0/s1
• InChI Key: ULZLIYVOYYQJRO-JIYCBSMMSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₀O₁₉
• Molecular Weight: 822.80 g/mol
• Exact Mass: 822.29462936 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -1.08
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• Epmedin C
• 110642-44-9
• 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• Baohuoside VI
• Baohuoside-VI
• Epimedin-C
• C39H50O19
• SCHEMBL2230230
• DTXSID90149351
• CHEBI:188298
• EX-A6785
• HY-N0260
• MFCD04039820
• s9269
• AKOS032962020
• CCG-270510
• CS-3678
• C39-H50-O19
• AS-56072
• A906383
• Q-100062
• 3-(((2S,3R,4R,5R,6S)-4,5-Dihydroxy-6-methyl-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-mannopyranosyl)oxy)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8585	85.85%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.5800	58.00%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9356	93.56%
P-glycoprotein inhibitior	+	0.6622	66.22%
P-glycoprotein substrate	+	0.5521	55.21%
CYP3A4 substrate	+	0.6773	67.73%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9306	93.06%
CYP2C9 inhibition	-	0.7318	73.18%
CYP2C19 inhibition	-	0.6575	65.75%
CYP2D6 inhibition	-	0.8183	81.83%
CYP1A2 inhibition	-	0.7072	70.72%
CYP2C8 inhibition	+	0.6933	69.33%
CYP inhibitory promiscuity	-	0.5487	54.87%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7378	73.78%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	+	0.5072	50.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7727	77.27%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8192	81.92%
Acute Oral Toxicity (c)	III	0.6326	63.26%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.6696	66.96%
Thyroid receptor binding	+	0.5522	55.22%
Glucocorticoid receptor binding	+	0.6291	62.91%
Aromatase binding	+	0.5706	57.06%
PPAR gamma	+	0.7164	71.64%
Honey bee toxicity	-	0.6792	67.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9668	96.68%

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	99.87%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.95%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.41%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.29%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.09%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.14%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.98%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	93.59%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.64%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.25%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.02%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.43%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.19%	97.36%
CHEMBL4208	P20618	Proteasome component C5	84.04%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.81%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.33%	95.89%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium brevicornu
• 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

Cross-Links

• PubChem: 5748394
• NPASS: NPC18355
• LOTUS: LTS0014819
• wikiData: Q72470910