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

Details

• Internal ID: 8c8758b5-e048-4a86-b98d-d2acdc8950f4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(4-hydroxyphenyl)methyl]chromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=C(C(=CC(=C4C3=O)O)O)CC5=CC=C(C=C5)O)C6=CC=C(C=C6)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[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(C(=CC(=C4C3=O)O)O)CC5=CC=C(C=C5)O)C6=CC=C(C=C6)O)CO)O)O)O)O)O
• InChI: InChI=1S/C33H34O16/c34-11-21-24(41)26(43)31(49-32-27(44)23(40)20(39)12-45-32)33(46-21)48-30-25(42)22-19(38)10-18(37)17(9-13-1-5-15(35)6-2-13)29(22)47-28(30)14-3-7-16(36)8-4-14/h1-8,10,20-21,23-24,26-27,31-41,43-44H,9,11-12H2/t20-,21-,23+,24-,26+,27-,31-,32+,33+/m1/s1
• InChI Key: NOTNCDZZFMJRKQ-RZBYRZLUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₄O₁₆
• Molecular Weight: 686.60 g/mol
• Exact Mass: 686.18468499 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -0.48
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9297	92.97%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5682	56.82%
OATP1B1 inhibitior	+	0.8659	86.59%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9338	93.38%
P-glycoprotein inhibitior	-	0.4596	45.96%
P-glycoprotein substrate	+	0.5122	51.22%
CYP3A4 substrate	+	0.6743	67.43%
CYP2C9 substrate	-	0.6487	64.87%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.7485	74.85%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9047	90.47%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.5909	59.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.8084	80.84%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6644	66.44%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9133	91.33%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8503	85.03%
Androgen receptor binding	+	0.7203	72.03%
Thyroid receptor binding	+	0.5156	51.56%
Glucocorticoid receptor binding	-	0.5358	53.58%
Aromatase binding	+	0.5880	58.80%
PPAR gamma	+	0.7545	75.45%
Honey bee toxicity	-	0.6165	61.65%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.51%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.07%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.14%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.78%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.21%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.79%	86.92%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.92%	95.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.02%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.98%	95.78%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.67%	95.50%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	89.63%	95.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.62%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.29%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.92%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.30%	95.83%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.10%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.72%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.40%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.28%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	83.90%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.78%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.40%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.81%	80.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.97%	97.28%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.87%	85.00%

Plants that contains it

• Spiranthes australis

Cross-Links

• PubChem: 25130458
• LOTUS: LTS0267691
• wikiData: Q105182772