Epimedin A1

Details

• Internal ID: 532cf8b7-ff8e-4274-a78f-9b442c28270d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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)O)OC6C(C(C(C(O6)CO)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)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C39H50O20/c1-14(2)5-10-18-20(54-37-30(49)28(47)25(44)21(12-40)55-37)11-19(42)23-27(46)36(33(57-34(18)23)16-6-8-17(52-4)9-7-16)59-39-32(51)35(24(43)15(3)53-39)58-38-31(50)29(48)26(45)22(13-41)56-38/h5-9,11,15,21-22,24-26,28-32,35,37-45,47-51H,10,12-13H2,1-4H3/t15-,21+,22+,24-,25+,26+,28-,29-,30+,31+,32+,35+,37+,38-,39-/m0/s1
• InChI Key: NLVBYGTTYRFJKH-YFNAFYFCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₀O₂₀
• Molecular Weight: 838.80 g/mol
• Exact Mass: 838.28954398 g/mol
• Topological Polar Surface Area (TPSA): 313.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -2.11
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

• 140147-77-9
• Hexandraside F
• 3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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
• HY-N0258
• AKOS037514634
• 3-[(6-Deoxy-3-O-beta-D-glucopyranosyl-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• AC-34094
• MS-31554
• CS-0008283
• Q-100151
• 3-(((2S,3R,4R,5S,6S)-3,5-Dihydroxy-6-methyl-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8164	81.64%
Caco-2	-	0.9141	91.41%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6461	64.61%
OATP2B1 inhibitior	-	0.5815	58.15%
OATP1B1 inhibitior	+	0.8763	87.63%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8902	89.02%
P-glycoprotein inhibitior	+	0.6609	66.09%
P-glycoprotein substrate	+	0.5420	54.20%
CYP3A4 substrate	+	0.6699	66.99%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9605	96.05%
CYP2C9 inhibition	-	0.7520	75.20%
CYP2C19 inhibition	-	0.6564	65.64%
CYP2D6 inhibition	-	0.8523	85.23%
CYP1A2 inhibition	-	0.7720	77.20%
CYP2C8 inhibition	+	0.6833	68.33%
CYP inhibitory promiscuity	-	0.5971	59.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7249	72.49%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.8116	81.16%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.5028	50.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7553	75.53%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7923	79.23%
Acute Oral Toxicity (c)	III	0.6499	64.99%
Estrogen receptor binding	+	0.8305	83.05%
Androgen receptor binding	+	0.6638	66.38%
Thyroid receptor binding	+	0.5405	54.05%
Glucocorticoid receptor binding	+	0.6170	61.70%
Aromatase binding	+	0.5587	55.87%
PPAR gamma	+	0.7224	72.24%
Honey bee toxicity	-	0.6952	69.52%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9594	95.94%

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	96.74%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.78%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.29%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.92%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.03%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	93.03%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	92.59%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.15%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.55%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.53%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.29%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.65%	86.92%
CHEMBL4208	P20618	Proteasome component C5	84.17%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.10%	92.94%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.73%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.05%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.43%	97.36%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• 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: 92043273
• NPASS: NPC57902