(3S)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[5-[(E)-3-hydroxyprop-1-enyl]-3-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propan-1-one

Details

• Internal ID: b7481482-0bad-4f1b-8096-81a16c4077e1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (3S)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[5-[(E)-3-hydroxyprop-1-enyl]-3-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propan-1-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)C(CC(=O)C3=CC(=C(C=C3)O)OC)O)C=CCO
• SMILES (Isomeric): COC1=CC(=CC(=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)[C@H](CC(=O)C3=CC(=C(C=C3)O)OC)O)/C=C/CO
• InChI: InChI=1S/C26H32O12/c1-35-19-10-14(5-6-16(19)29)17(30)11-18(31)15-8-13(4-3-7-27)9-20(36-2)25(15)38-26-24(34)23(33)22(32)21(12-28)37-26/h3-6,8-10,18,21-24,26-29,31-34H,7,11-12H2,1-2H3/b4-3+/t18-,21+,22+,23-,24+,26-/m0/s1
• InChI Key: SWUYIHFWXBMJBL-KQNQHNSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.10
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6119	61.19%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5609	56.09%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.8734	87.34%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8242	82.42%
P-glycoprotein inhibitior	-	0.4335	43.35%
P-glycoprotein substrate	-	0.6698	66.98%
CYP3A4 substrate	+	0.6360	63.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8267	82.67%
CYP3A4 inhibition	-	0.8311	83.11%
CYP2C9 inhibition	-	0.9357	93.57%
CYP2C19 inhibition	-	0.9221	92.21%
CYP2D6 inhibition	-	0.8871	88.71%
CYP1A2 inhibition	-	0.8835	88.35%
CYP2C8 inhibition	+	0.7128	71.28%
CYP inhibitory promiscuity	-	0.7954	79.54%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7539	75.39%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9329	93.29%
Skin irritation	-	0.8407	84.07%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6929	69.29%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8494	84.94%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6841	68.41%
Acute Oral Toxicity (c)	III	0.7797	77.97%
Estrogen receptor binding	+	0.8554	85.54%
Androgen receptor binding	+	0.5759	57.59%
Thyroid receptor binding	+	0.5721	57.21%
Glucocorticoid receptor binding	+	0.5993	59.93%
Aromatase binding	-	0.5087	50.87%
PPAR gamma	+	0.6347	63.47%
Honey bee toxicity	-	0.7427	74.27%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7729	77.29%

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	99.37%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.93%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.48%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.35%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.89%	86.33%
CHEMBL3194	P02766	Transthyretin	89.80%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	89.13%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.69%	89.62%
CHEMBL4208	P20618	Proteasome component C5	83.36%	90.00%
CHEMBL2581	P07339	Cathepsin D	82.96%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.64%	95.89%
CHEMBL1873	P00750	Tissue-type plasminogen activator	82.10%	93.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.00%	96.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.57%	95.83%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.04%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.79%	97.14%
CHEMBL2535	P11166	Glucose transporter	80.41%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.29%	97.09%

Plants that contains it

• Bidens parviflora

Cross-Links

• PubChem: 162897595
• LOTUS: LTS0168320
• wikiData: Q105262912