3-[(2S,3S,5R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one

Details

• Internal ID: 8c72d851-1ff2-4245-b560-b241d7e26665
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3S,5R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): CC1[C@@H](C([C@@H]([C@@H](O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)O)O[C@H]5[C@@H](C([C@@H](C(O5)CO)O)O)O)O)O
• InChI: InChI=1S/C32H38O15/c1-12(2)4-9-16-17(35)10-18(36)20-23(39)29(27(45-28(16)20)14-5-7-15(34)8-6-14)46-32-30(25(41)21(37)13(3)43-32)47-31-26(42)24(40)22(38)19(11-33)44-31/h4-8,10,13,19,21-22,24-26,30-38,40-42H,9,11H2,1-3H3/t13?,19?,21-,22+,24?,25?,26+,30-,31-,32-/m0/s1
• InChI Key: FWINXQRXURMYOG-PAGOZVFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₅
• Molecular Weight: 662.60 g/mol
• Exact Mass: 662.22107050 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.12
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• LMPK12111713

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8664	86.64%
Caco-2	-	0.9193	91.93%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7171	71.71%
OATP2B1 inhibitior	-	0.7141	71.41%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9029	90.29%
P-glycoprotein inhibitior	-	0.4567	45.67%
P-glycoprotein substrate	+	0.5260	52.60%
CYP3A4 substrate	+	0.6602	66.02%
CYP2C9 substrate	-	0.6532	65.32%
CYP2D6 substrate	-	0.8528	85.28%
CYP3A4 inhibition	-	0.9436	94.36%
CYP2C9 inhibition	-	0.7241	72.41%
CYP2C19 inhibition	-	0.6819	68.19%
CYP2D6 inhibition	-	0.8386	83.86%
CYP1A2 inhibition	-	0.6373	63.73%
CYP2C8 inhibition	+	0.7174	71.74%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7420	74.20%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.5428	54.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.3972	39.72%
Micronuclear	-	0.5367	53.67%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8659	86.59%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8308	83.08%
Acute Oral Toxicity (c)	III	0.6098	60.98%
Estrogen receptor binding	+	0.8488	84.88%
Androgen receptor binding	+	0.7054	70.54%
Thyroid receptor binding	+	0.5340	53.40%
Glucocorticoid receptor binding	+	0.6661	66.61%
Aromatase binding	+	0.6455	64.55%
PPAR gamma	+	0.7322	73.22%
Honey bee toxicity	-	0.6560	65.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	99.79%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.89%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.20%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.52%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	95.93%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.33%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.32%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.51%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.33%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.93%	95.64%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.30%	91.38%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.33%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.93%	86.92%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.82%	93.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.80%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.64%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	83.99%	94.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.24%	91.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.95%	97.36%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.60%	95.78%

Plants that contains it

• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum

Cross-Links

• PubChem: 44258785
• NPASS: NPC77284
• LOTUS: LTS0179866
• wikiData: Q104393847