7-[(2S,3R,4S,5S,6R)-3-[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: 10b2cda6-0319-4157-b2be-db4551cc9004
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-3-[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@H]([C@](CO5)(CO)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-37-17-4-11(2-3-13(17)30)16-7-15(32)20-14(31)5-12(6-18(20)40-16)39-25-23(22(34)21(33)19(8-28)41-25)42-26-24(35)27(36,9-29)10-38-26/h2-7,19,21-26,28-31,33-36H,8-10H2,1H3/t19-,21-,22+,23-,24-,25-,26+,27-/m1/s1
• InChI Key: GYQQQCVFOLKXGH-XWEJYCMRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6754	67.54%
Caco-2	-	0.9013	90.13%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6254	62.54%
OATP2B1 inhibitior	-	0.7070	70.70%
OATP1B1 inhibitior	+	0.9274	92.74%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5849	58.49%
P-glycoprotein inhibitior	-	0.4874	48.74%
P-glycoprotein substrate	+	0.5523	55.23%
CYP3A4 substrate	+	0.6761	67.61%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.8296	82.96%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	+	0.7260	72.60%
CYP inhibitory promiscuity	-	0.7811	78.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5250	52.50%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9121	91.21%
Skin irritation	-	0.8131	81.31%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	+	0.5208	52.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6960	69.60%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8821	88.21%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7969	79.69%
Acute Oral Toxicity (c)	III	0.6985	69.85%
Estrogen receptor binding	+	0.8499	84.99%
Androgen receptor binding	+	0.6386	63.86%
Thyroid receptor binding	+	0.5462	54.62%
Glucocorticoid receptor binding	+	0.6078	60.78%
Aromatase binding	+	0.7468	74.68%
PPAR gamma	+	0.7829	78.29%
Honey bee toxicity	-	0.6638	66.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.6644	66.44%

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	99.66%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.31%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.70%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.45%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.26%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.79%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.89%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.48%	86.92%
CHEMBL220	P22303	Acetylcholinesterase	91.79%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.60%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.77%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.78%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.74%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.14%	92.94%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.75%	97.28%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.05%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.10%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.06%	96.21%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.06%	94.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.78%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.63%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.32%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.87%	95.83%
CHEMBL4208	P20618	Proteasome component C5	82.39%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.35%	95.53%
CHEMBL226	P30542	Adenosine A1 receptor	80.34%	95.93%
CHEMBL1907	P15144	Aminopeptidase N	80.22%	93.31%

Plants that contains it

• Apium graveolens

Cross-Links

• PubChem: 71718203
• LOTUS: LTS0049349
• wikiData: Q105024049