5,8-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-7-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Details

• Internal ID: 94f26f25-3ce9-4fdf-89f5-0af1309c7008
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,8-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C3=C(C(=C2)O)C(=O)C(=C(O3)C4=CC=C(C=C4)O)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C3=C(C(=C2)O)C(=O)C(=C(O3)C4=CC=C(C=C4)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-15(31)19(35)21(37)26(39-8)40-12-6-11(30)14-18(34)25(43-27-22(38)20(36)16(32)13(7-28)41-27)23(42-24(14)17(12)33)9-2-4-10(29)5-3-9/h2-6,8,13,15-16,19-22,26-33,35-38H,7H2,1H3/t8-,13+,15-,16+,19+,20-,21+,22+,26-,27-/m0/s1
• InChI Key: QYECIBJZFSVSHH-CPBWYJGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 5,8-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-7-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 5,8-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9173	91.73%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5591	55.91%
OATP1B1 inhibitior	+	0.8776	87.76%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8068	80.68%
P-glycoprotein inhibitior	-	0.5491	54.91%
P-glycoprotein substrate	-	0.5932	59.32%
CYP3A4 substrate	+	0.6196	61.96%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.7405	74.05%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8871	88.71%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5172	51.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7696	76.96%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8017	80.17%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7822	78.22%
Androgen receptor binding	+	0.5999	59.99%
Thyroid receptor binding	-	0.5510	55.10%
Glucocorticoid receptor binding	+	0.6041	60.41%
Aromatase binding	+	0.5265	52.65%
PPAR gamma	+	0.6822	68.22%
Honey bee toxicity	-	0.7628	76.28%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.24%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.09%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.14%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.32%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.53%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	89.72%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.53%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.31%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.21%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.20%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.11%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.07%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.47%	85.14%
CHEMBL3194	P02766	Transthyretin	84.81%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.42%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	84.39%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.14%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.28%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.47%	90.71%

Plants that contains it

• Sedum sarmentosum
• Sinocrassula indica

Cross-Links

• PubChem: 25112363
• LOTUS: LTS0106264
• wikiData: Q105230066