3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-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

Details

• Internal ID: a1d919ae-88e1-4ae0-a39c-4a466350e15d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-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)C6=CC=C(C=C6)OC)CO)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)C6=CC=C(C=C6)OC)CO)O)O)O)O)O
• InChI: InChI=1S/C39H50O19/c1-15(2)5-10-19-21(53-38-32(50)29(47)26(44)22(13-40)54-38)12-11-20-25(43)35(33(56-34(19)20)17-6-8-18(51-4)9-7-17)57-39-36(30(48)27(45)23(14-41)55-39)58-37-31(49)28(46)24(42)16(3)52-37/h5-9,11-12,16,22-24,26-32,36-42,44-50H,10,13-14H2,1-4H3/t16-,22+,23+,24-,26+,27+,28+,29-,30-,31+,32+,36+,37-,38+,39-/m0/s1
• InChI Key: NSNVPRPWHAWADT-FAWIOFLOSA-N
• Popularity: 7 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: -0.10
• Atomic LogP (AlogP): -1.81
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 12

Synonyms

• Q-100060

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8164	81.64%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6461	64.61%
OATP2B1 inhibitior	-	0.5846	58.46%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9624	96.24%
P-glycoprotein inhibitior	+	0.6802	68.02%
P-glycoprotein substrate	+	0.5585	55.85%
CYP3A4 substrate	+	0.6781	67.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8258	82.58%
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	+	0.6580	65.80%
CYP inhibitory promiscuity	-	0.5971	59.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7249	72.49%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.8116	81.16%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8611	86.11%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7668	76.68%
Acute Oral Toxicity (c)	III	0.6499	64.99%
Estrogen receptor binding	+	0.8123	81.23%
Androgen receptor binding	+	0.6742	67.42%
Thyroid receptor binding	+	0.5448	54.48%
Glucocorticoid receptor binding	+	0.6248	62.48%
Aromatase binding	+	0.5608	56.08%
PPAR gamma	+	0.7166	71.66%
Honey bee toxicity	-	0.6940	69.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
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	99.34%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.88%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.95%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.08%	89.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.73%	83.57%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.13%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.12%	96.00%
CHEMBL2581	P07339	Cathepsin D	92.11%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.86%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.85%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.12%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.34%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.19%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.54%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.22%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.86%	95.89%

Plants that contains it

• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium sagittatum
• Vancouveria hexandra

Cross-Links

• PubChem: 11972345
• LOTUS: LTS0092001
• wikiData: Q105185160