2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Details

• Internal ID: b33a37ff-8141-425f-a68e-6264596c8d4b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O23/c34-5-13-17(40)21(44)24(47)31(51-13)50-7-15-19(42)23(46)26(49)33(53-15)56-30-20(43)16-11(38)4-12(39)28(55-32-25(48)22(45)18(41)14(6-35)52-32)29(16)54-27(30)8-1-2-9(36)10(37)3-8/h1-4,13-15,17-19,21-26,31-42,44-49H,5-7H2/t13-,14-,15-,17-,18-,19-,21+,22+,23+,24-,25-,26-,31-,32+,33+/m1/s1
• InChI Key: JKKXWHFCHUTGCO-RPZGNCTFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₃
• Molecular Weight: 804.70 g/mol
• Exact Mass: 804.19603752 g/mol
• Topological Polar Surface Area (TPSA): 385.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -5.54
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9051	90.51%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.7091	70.91%
OATP1B1 inhibitior	+	0.9218	92.18%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7351	73.51%
P-glycoprotein inhibitior	+	0.6179	61.79%
P-glycoprotein substrate	-	0.7423	74.23%
CYP3A4 substrate	+	0.5994	59.94%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.6806	68.06%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8977	89.77%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7844	78.44%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.5446	54.46%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7320	73.20%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.6433	64.33%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6556	65.56%
Aromatase binding	+	0.5411	54.11%
PPAR gamma	+	0.7231	72.31%
Honey bee toxicity	-	0.7350	73.50%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.75%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.00%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.82%	99.15%
CHEMBL2581	P07339	Cathepsin D	93.39%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.48%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.26%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.08%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.86%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	85.53%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.92%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.94%	97.09%
CHEMBL3194	P02766	Transthyretin	81.72%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.43%	96.09%

Plants that contains it

• Phedimus kamtschaticus
• Rhododendron dauricum
• Rhododendron micranthum
• Rhododendron mucronatum
• Rhododendron mucronulatum

Cross-Links

• PubChem: 11968523
• NPASS: NPC13401