2-(4-Hydroxyphenyl)-5-hydroxy-7-[2-O-[5-O-[(E)-3-methoxy-4-hydroxycinnamoyl]-D-apio-beta-D-furanosyl]-beta-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

Details

• Internal ID: dbe40c7b-b5c2-4f33-9118-9a15b7ea64b9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2(COC(C2O)OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)O)O)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@]2(CO[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)O)O)CO)O)O)O)O
• InChI: InChI=1S/C36H36O17/c1-47-25-10-17(2-8-21(25)39)3-9-28(42)48-15-36(46)16-49-35(33(36)45)53-32-31(44)30(43)27(14-37)52-34(32)50-20-11-22(40)29-23(41)13-24(51-26(29)12-20)18-4-6-19(38)7-5-18/h2-13,27,30-35,37-40,43-46H,14-16H2,1H3/b9-3+/t27-,30-,31+,32-,33+,34-,35+,36-/m1/s1
• InChI Key: CNNDXKQLSAQYHQ-DQPLZYKKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆O₁₇
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.19524968 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• 2-(4-Hydroxyphenyl)-5-hydroxy-7-[2-O-[5-O-[(E)-3-methoxy-4-hydroxycinnamoyl]-D-apio-beta-D-furanosyl]-beta-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7084	70.84%
Caco-2	-	0.8878	88.78%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5890	58.90%
OATP2B1 inhibitior	-	0.7107	71.07%
OATP1B1 inhibitior	+	0.8952	89.52%
OATP1B3 inhibitior	+	0.9744	97.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4664	46.64%
P-glycoprotein inhibitior	+	0.6720	67.20%
P-glycoprotein substrate	+	0.6453	64.53%
CYP3A4 substrate	+	0.7109	71.09%
CYP2C9 substrate	-	0.8150	81.50%
CYP2D6 substrate	-	0.8672	86.72%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.8388	83.88%
CYP2C19 inhibition	-	0.8253	82.53%
CYP2D6 inhibition	-	0.9123	91.23%
CYP1A2 inhibition	-	0.9178	91.78%
CYP2C8 inhibition	+	0.8419	84.19%
CYP inhibitory promiscuity	-	0.7981	79.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4932	49.32%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.8099	80.99%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5728	57.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.3640	36.40%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9324	93.24%
Acute Oral Toxicity (c)	III	0.6079	60.79%
Estrogen receptor binding	+	0.8154	81.54%
Androgen receptor binding	+	0.7354	73.54%
Thyroid receptor binding	+	0.5271	52.71%
Glucocorticoid receptor binding	+	0.6258	62.58%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.7328	73.28%
Honey bee toxicity	-	0.6502	65.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8698	86.98%

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	99.88%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.73%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.13%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.63%	94.45%
CHEMBL3194	P02766	Transthyretin	95.08%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.05%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.79%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.96%	96.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	93.41%	97.28%
CHEMBL1951	P21397	Monoamine oxidase A	93.40%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.68%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.31%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.36%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	88.09%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.26%	99.15%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.55%	94.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.37%	95.78%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.20%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.79%	86.92%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	84.60%	97.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.35%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.34%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.06%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.48%	99.17%
CHEMBL4208	P20618	Proteasome component C5	82.36%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.34%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.93%	96.21%
CHEMBL340	P08684	Cytochrome P450 3A4	80.86%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	80.29%	92.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.23%	91.71%

Plants that contains it

• Apium graveolens

Cross-Links

• PubChem: 44478942
• NPASS: NPC199172
• LOTUS: LTS0117576
• wikiData: Q104966016