[(2R,3S,4S,5R,6S)-6-[4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy]-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 40c05597-8138-4627-81b4-8f819fc73bb2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxyphenoxy]-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxyoxan-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(C(=C(C=C3)C(=O)C=CC4=CC(=C(C=C4)O)O)O)O)OC(=O)C=CC5=CC(=C(C=C5)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(C(=C(C=C3)C(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)OC(=O)/C=C/C5=CC(=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C39H34O16/c40-23-8-1-20(2-9-23)6-15-32(46)52-19-31-36(50)37(51)38(55-33(47)16-7-22-5-13-27(43)29(45)18-22)39(54-31)53-30-14-10-24(34(48)35(30)49)25(41)11-3-21-4-12-26(42)28(44)17-21/h1-18,31,36-40,42-45,48-51H,19H2/b11-3+,15-6+,16-7+/t31-,36-,37+,38-,39-/m1/s1
• InChI Key: VZXQHTJVWMHMSB-STAAEYCOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₄O₁₆
• Molecular Weight: 758.70 g/mol
• Exact Mass: 758.18468499 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5424	54.24%
Caco-2	-	0.8913	89.13%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7739	77.39%
OATP2B1 inhibitior	-	0.7037	70.37%
OATP1B1 inhibitior	+	0.8797	87.97%
OATP1B3 inhibitior	+	0.9244	92.44%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8636	86.36%
P-glycoprotein inhibitior	+	0.7145	71.45%
P-glycoprotein substrate	-	0.7040	70.40%
CYP3A4 substrate	+	0.6358	63.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8743	87.43%
CYP3A4 inhibition	-	0.8905	89.05%
CYP2C9 inhibition	-	0.6459	64.59%
CYP2C19 inhibition	-	0.7576	75.76%
CYP2D6 inhibition	-	0.9124	91.24%
CYP1A2 inhibition	-	0.8574	85.74%
CYP2C8 inhibition	+	0.8445	84.45%
CYP inhibitory promiscuity	-	0.7989	79.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6875	68.75%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8928	89.28%
Skin irritation	-	0.8366	83.66%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6735	67.35%
Micronuclear	+	0.6666	66.66%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8125	81.25%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9629	96.29%
Acute Oral Toxicity (c)	III	0.6825	68.25%
Estrogen receptor binding	+	0.7436	74.36%
Androgen receptor binding	+	0.7548	75.48%
Thyroid receptor binding	+	0.5658	56.58%
Glucocorticoid receptor binding	-	0.4806	48.06%
Aromatase binding	-	0.5083	50.83%
PPAR gamma	+	0.6988	69.88%
Honey bee toxicity	-	0.7431	74.31%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9713	97.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.33%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.30%	91.11%
CHEMBL3194	P02766	Transthyretin	98.66%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.43%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.29%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.19%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.73%	96.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.71%	80.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.77%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.49%	97.09%
CHEMBL4208	P20618	Proteasome component C5	88.29%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.57%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.20%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.61%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.18%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.76%	89.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.86%	89.62%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.93%	83.00%

Plants that contains it

• Bidens frondosa

Cross-Links

• PubChem: 15755766
• LOTUS: LTS0170937
• wikiData: Q105300034