5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy)-1-benzopyran-4-one

Details

• Internal ID: 835f2591-04b5-43f2-9b46-5f8857096037
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(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-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=C(C=C6)O)OC)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=C(C=C6)O)OC)O)O)O)O)O)O
• InChI: InChI=1S/C34H42O21/c1-10-20(38)24(42)27(45)32(50-10)49-9-18-22(40)26(44)29(47)34(54-18)55-31-23(41)19-14(37)6-12(51-33-28(46)25(43)21(39)17(8-35)53-33)7-16(19)52-30(31)11-3-4-13(36)15(5-11)48-2/h3-7,10,17-18,20-22,24-29,32-40,42-47H,8-9H2,1-2H3/t10-,17+,18+,20-,21+,22+,24+,25-,26-,27+,28+,29+,32+,33+,34-/m0/s1
• InChI Key: VLDJCNQOIAEWHD-OBQKRMBVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₂₁
• Molecular Weight: 786.70 g/mol
• Exact Mass: 786.22185834 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -3.91
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

• Isorhamnetin-3-O-rutinoside-7-O-glucoside
• 5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy)-1-benzopyran-4-one
• 4H-1-BEnzopyran-4-one, 3-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-
• 5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-[3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-1-benzopyran-4-one
• auriculatin 4'A</=-O-glucoside
• DTXSID30970828
• FS-8555
• 3-{[6-O-(6-Deoxyhexopyranosyl)hexopyranosyl]oxy}-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl hexopyranoside
• 4H-1-BEnzopyran-4-one,3-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-
• 5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5623	56.23%
Caco-2	-	0.9117	91.17%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.5789	57.89%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.9748	97.48%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7700	77.00%
P-glycoprotein inhibitior	-	0.4425	44.25%
P-glycoprotein substrate	+	0.6082	60.82%
CYP3A4 substrate	+	0.6377	63.77%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
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	+	0.8157	81.57%
CYP inhibitory promiscuity	-	0.7113	71.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	-	0.6692	66.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.7872	78.72%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8782	87.82%
Acute Oral Toxicity (c)	III	0.7041	70.41%
Estrogen receptor binding	+	0.7924	79.24%
Androgen receptor binding	-	0.4832	48.32%
Thyroid receptor binding	-	0.4916	49.16%
Glucocorticoid receptor binding	+	0.5631	56.31%
Aromatase binding	+	0.5533	55.33%
PPAR gamma	+	0.7242	72.42%
Honey bee toxicity	-	0.7369	73.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
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	97.55%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.84%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.20%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.46%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.27%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.02%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	92.14%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.82%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.02%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	89.34%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.90%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.08%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.22%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.61%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.19%	95.78%
CHEMBL3194	P02766	Transthyretin	82.66%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.75%	95.89%
CHEMBL1907	P15144	Aminopeptidase N	80.39%	93.31%
CHEMBL4208	P20618	Proteasome component C5	80.34%	90.00%
CHEMBL220	P22303	Acetylcholinesterase	80.12%	94.45%

Plants that contains it

• Coleogyne ramosissima

Cross-Links

• PubChem: 5481665
• LOTUS: LTS0107706
• wikiData: Q82954090