[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 021a0a60-8c30-42e1-8e44-017931aed6bb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• InChI: InChI=1S/C36H36O19/c37-12-22-26(43)29(46)31(48)35(53-22)51-17-10-20(41)25-21(11-17)52-33(15-4-7-18(39)19(40)9-15)34(28(25)45)55-36-32(49)30(47)27(44)23(54-36)13-50-24(42)8-3-14-1-5-16(38)6-2-14/h1-11,22-23,26-27,29-32,35-41,43-44,46-49H,12-13H2/b8-3+/t22-,23-,26-,27-,29+,30+,31-,32-,35-,36+/m1/s1
• InChI Key: VASHBWYFPVZWGX-ZTALYCNZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆O₁₉
• Molecular Weight: 772.70 g/mol
• Exact Mass: 772.18507891 g/mol
• Topological Polar Surface Area (TPSA): 312.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5570	55.70%
Caco-2	-	0.8949	89.49%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5040	50.40%
OATP2B1 inhibitior	-	0.5691	56.91%
OATP1B1 inhibitior	+	0.9006	90.06%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6671	66.71%
P-glycoprotein inhibitior	+	0.6811	68.11%
P-glycoprotein substrate	-	0.6009	60.09%
CYP3A4 substrate	+	0.6749	67.49%
CYP2C9 substrate	-	0.8109	81.09%
CYP2D6 substrate	-	0.8693	86.93%
CYP3A4 inhibition	-	0.9209	92.09%
CYP2C9 inhibition	-	0.8990	89.90%
CYP2C19 inhibition	-	0.8708	87.08%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.9325	93.25%
CYP2C8 inhibition	+	0.8864	88.64%
CYP inhibitory promiscuity	-	0.7843	78.43%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6850	68.50%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.8335	83.35%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7036	70.36%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9032	90.32%
Acute Oral Toxicity (c)	IV	0.4410	44.10%
Estrogen receptor binding	+	0.7578	75.78%
Androgen receptor binding	+	0.6953	69.53%
Thyroid receptor binding	+	0.5454	54.54%
Glucocorticoid receptor binding	+	0.5533	55.33%
Aromatase binding	+	0.5283	52.83%
PPAR gamma	+	0.6790	67.90%
Honey bee toxicity	-	0.6886	68.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9324	93.24%

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	99.72%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.63%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.26%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.75%	86.33%
CHEMBL3194	P02766	Transthyretin	95.11%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.15%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.83%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.57%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.33%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.17%	96.00%
CHEMBL2581	P07339	Cathepsin D	91.02%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.25%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.89%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.72%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.51%	95.78%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.79%	80.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.91%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.41%	91.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.93%	85.14%
CHEMBL242	Q92731	Estrogen receptor beta	80.57%	98.35%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.08%	95.83%

Plants that contains it

• Lotus polyphyllos

Cross-Links

• PubChem: 11968878
• LOTUS: LTS0229716
• wikiData: Q105282951