3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxychromen-4-one

Details

• Internal ID: c8594d06-5884-4074-876f-feb2d586a8a3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C29H34O18/c1-41-13-5-9(3-4-10(13)32)23-26(19(37)16-11(33)6-12(34)24(42-2)25(16)45-23)46-29-27(21(39)18(36)15(8-31)44-29)47-28-22(40)20(38)17(35)14(7-30)43-28/h3-6,14-15,17-18,20-22,27-36,38-40H,7-8H2,1-2H3/t14-,15-,17-,18-,20+,21+,22-,27-,28+,29+/m0/s1
• InChI Key: XVMFKSYZWYZRFY-DGYZMVBVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₈
• Molecular Weight: 670.60 g/mol
• Exact Mass: 670.17451423 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.40
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5623	56.23%
Caco-2	-	0.9052	90.52%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.5820	58.20%
OATP1B1 inhibitior	+	0.9117	91.17%
OATP1B3 inhibitior	+	0.9748	97.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6463	64.63%
P-glycoprotein inhibitior	-	0.4662	46.62%
P-glycoprotein substrate	-	0.6114	61.14%
CYP3A4 substrate	+	0.6376	63.76%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.9208	92.08%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.6893	68.93%
CYP inhibitory promiscuity	-	0.7113	71.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5072	50.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.3733	37.33%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8421	84.21%
Acute Oral Toxicity (c)	III	0.7041	70.41%
Estrogen receptor binding	+	0.8502	85.02%
Androgen receptor binding	+	0.6239	62.39%
Thyroid receptor binding	-	0.5101	51.01%
Glucocorticoid receptor binding	+	0.5777	57.77%
Aromatase binding	+	0.6363	63.63%
PPAR gamma	+	0.7348	73.48%
Honey bee toxicity	-	0.7395	73.95%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7167	71.67%

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	99.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.61%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.37%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.00%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.52%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.24%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.72%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.00%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.84%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	87.25%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.20%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.18%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.61%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.54%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.30%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.46%	95.89%

Plants that contains it

• Paeonia tenuifolia

Cross-Links

• PubChem: 162911857
• LOTUS: LTS0247978
• wikiData: Q105342969