Epimedin B

Details

• Internal ID: 8b64f885-b722-4113-b7cc-8f7cead4161b
• 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,4S,5R)-3,4,5-trihydroxyoxan-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)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)OC6C(C(C(CO6)O)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)OC)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O
• InChI: InChI=1S/C38H48O19/c1-14(2)5-10-18-21(53-37-31(49)28(46)26(44)22(12-39)54-37)11-19(40)23-27(45)34(32(55-33(18)23)16-6-8-17(50-4)9-7-16)56-38-35(29(47)24(42)15(3)52-38)57-36-30(48)25(43)20(41)13-51-36/h5-9,11,15,20,22,24-26,28-31,35-44,46-49H,10,12-13H2,1-4H3/t15-,20+,22+,24-,25-,26+,28-,29+,30+,31+,35+,36-,37+,38-/m0/s1
• InChI Key: OCZZCFAOOWZSRX-LRHLXKJSSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₈O₁₉
• Molecular Weight: 808.80 g/mol
• Exact Mass: 808.27897930 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.47
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• Epmedin B
• 110623-73-9
• 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-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
• Epimedin-B
• C38H48O19
• SCHEMBL3674180
• DTXSID40149341
• CHEBI:169048
• EX-A6792
• HY-N0259
• s9268
• AKOS016002028
• AC-6040
• CCG-270501
• CS-3677
• C38-H48-O19
• MS-31497
• A894871
• Q-100061
• 3-[(6-Deoxy-2-O-beta-D-xylopyranosyl-alpha-L-mannopyranosyloxy)]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxy-phenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-2-O-beta-D-xylopyranosyl-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	+	0.8517	85.17%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5827	58.27%
OATP2B1 inhibitior	-	0.7201	72.01%
OATP1B1 inhibitior	+	0.8719	87.19%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9182	91.82%
P-glycoprotein inhibitior	+	0.6589	65.89%
P-glycoprotein substrate	+	0.6480	64.80%
CYP3A4 substrate	+	0.6993	69.93%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9509	95.09%
CYP2C9 inhibition	-	0.8184	81.84%
CYP2C19 inhibition	-	0.7492	74.92%
CYP2D6 inhibition	-	0.8313	83.13%
CYP1A2 inhibition	-	0.7718	77.18%
CYP2C8 inhibition	+	0.7017	70.17%
CYP inhibitory promiscuity	-	0.7704	77.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7219	72.19%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9093	90.93%
Skin irritation	-	0.8033	80.33%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	+	0.5172	51.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.8035	80.35%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.8573	85.73%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9306	93.06%
Acute Oral Toxicity (c)	III	0.6514	65.14%
Estrogen receptor binding	+	0.8198	81.98%
Androgen receptor binding	+	0.6339	63.39%
Thyroid receptor binding	+	0.5482	54.82%
Glucocorticoid receptor binding	+	0.6131	61.31%
Aromatase binding	+	0.5742	57.42%
PPAR gamma	+	0.7241	72.41%
Honey bee toxicity	-	0.6693	66.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9413	94.13%

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	99.93%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.86%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.11%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.30%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.87%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.98%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.35%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.83%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.51%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.32%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.69%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.51%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.74%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.23%	92.94%
CHEMBL4208	P20618	Proteasome component C5	87.73%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.08%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.75%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.68%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.13%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	81.69%	94.75%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium hunanense
• 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: 5748393
• NPASS: NPC85072
• LOTUS: LTS0249709
• wikiData: Q72470907