5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one

Details

• Internal ID: 597efc7f-c1a0-4391-849b-f97f300e161d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC4C(C(C(CO4)O)O)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(C=C(C=C3O2)O[C@@H]4[C@H]([C@H]([C@H](CO4)O)O)O)O)O[C@H]5[C@@H]([C@@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-38-14-4-9(2-3-11(14)29)24-25(43-27-23(37)21(35)19(33)16(7-28)42-27)20(34)17-12(30)5-10(6-15(17)41-24)40-26-22(36)18(32)13(31)8-39-26/h2-6,13,16,18-19,21-23,26-33,35-37H,7-8H2,1H3/t13-,16+,18-,19+,21+,22-,23+,26+,27-/m0/s1
• InChI Key: JZHGXZBWVCUGTF-QLYWULHSSA-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): 255.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.12
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4761	47.61%
Caco-2	-	0.9172	91.72%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7210	72.10%
P-glycoprotein inhibitior	-	0.5072	50.72%
P-glycoprotein substrate	-	0.5371	53.71%
CYP3A4 substrate	+	0.6628	66.28%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9488	94.88%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	+	0.7768	77.68%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8999	89.99%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.5008	50.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7697	76.97%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9414	94.14%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	+	0.5933	59.33%
Thyroid receptor binding	-	0.5576	55.76%
Glucocorticoid receptor binding	+	0.5960	59.60%
Aromatase binding	-	0.4921	49.21%
PPAR gamma	+	0.6656	66.56%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	-	0.4193	41.93%

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	99.46%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.16%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.79%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.74%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	94.98%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.84%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.99%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.87%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.26%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.40%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.14%	86.92%
CHEMBL4208	P20618	Proteasome component C5	86.78%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.89%	95.78%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.38%	95.53%
CHEMBL3401	O75469	Pregnane X receptor	84.15%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.13%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.93%	96.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.91%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.71%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.54%	95.83%
CHEMBL1951	P21397	Monoamine oxidase A	83.24%	91.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.66%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.30%	92.62%

Plants that contains it

• Heuchera micrantha

Cross-Links

• PubChem: 163104669
• LOTUS: LTS0264398
• wikiData: Q105137402