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

Details

• Internal ID: 97a81340-094f-4a35-9d1b-eabbdd9bef2e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-7-15-19(32)22(35)24(37)26(42-15)39-8-16-20(33)23(36)25(38)27(43-16)41-14-6-13-17(21(34)18(14)31)11(30)5-12(40-13)9-1-3-10(29)4-2-9/h1-6,15-16,19-20,22-29,31-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25-,26-,27-/m1/s1
• InChI Key: FMAMQXFWLVEYMA-IJTBWITGSA-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: -1.60
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

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	-	0.9227	92.27%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5571	55.71%
OATP1B1 inhibitior	+	0.7809	78.09%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6228	62.28%
P-glycoprotein inhibitior	-	0.6506	65.06%
P-glycoprotein substrate	-	0.6772	67.72%
CYP3A4 substrate	+	0.6050	60.50%
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	+	0.7836	78.36%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6892	68.92%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8446	84.46%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8410	84.10%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7515	75.15%
Androgen receptor binding	+	0.6673	66.73%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5165	51.65%
Aromatase binding	+	0.6192	61.92%
PPAR gamma	+	0.7179	71.79%
Honey bee toxicity	-	0.6534	65.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6049	60.49%
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	99.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.19%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.69%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.03%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.46%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.36%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.09%	86.92%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.82%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.83%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.81%	95.78%
CHEMBL3194	P02766	Transthyretin	90.39%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	89.36%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.08%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.49%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.12%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.03%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.66%	95.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.35%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.18%	99.15%

Plants that contains it

• Helichrysum arenarium
• Hypericum ascyron

Cross-Links

• PubChem: 162897126
• LOTUS: LTS0141272
• wikiData: Q105151552