[6-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: d2ce1c78-1601-453b-be18-64a55624896c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2
• InChI Key: DVGGLGXQSFURLP-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₃
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.13734088 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 22153-44-2
• FT-0775452
• FT-0776716

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4689	46.89%
Caco-2	-	0.9079	90.79%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5846	58.46%
OATP2B1 inhibitior	-	0.5538	55.38%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6083	60.83%
P-glycoprotein inhibitior	+	0.6362	63.62%
P-glycoprotein substrate	-	0.6383	63.83%
CYP3A4 substrate	+	0.6539	65.39%
CYP2C9 substrate	-	0.8105	81.05%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.9312	93.12%
CYP2C8 inhibition	+	0.9057	90.57%
CYP inhibitory promiscuity	-	0.7755	77.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6770	67.70%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8942	89.42%
Skin irritation	-	0.8069	80.69%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5223	52.23%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9133	91.33%
Acute Oral Toxicity (c)	III	0.4048	40.48%
Estrogen receptor binding	+	0.7546	75.46%
Androgen receptor binding	+	0.8237	82.37%
Thyroid receptor binding	-	0.4878	48.78%
Glucocorticoid receptor binding	+	0.6653	66.53%
Aromatase binding	+	0.5493	54.93%
PPAR gamma	+	0.6980	69.80%
Honey bee toxicity	-	0.7564	75.64%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9677	96.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2326	P43166	Carbonic anhydrase VII	4.6 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	134.3 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.33%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.44%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	97.93%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.67%	86.33%
CHEMBL3194	P02766	Transthyretin	96.26%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	95.54%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.02%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.76%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.43%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.85%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.91%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.95%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.33%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.57%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.48%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.36%	95.50%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.76%	96.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.34%	94.00%

Plants that contains it

• Aerva lanata
• Agrimonia eupatoria
• Agrimonia pilosa
• Anaphalis lactea
• Anaphalis margaritacea
• Anaphalis sinica
• Aruncus dioicus
• Castanea sativa
• Croton gratissimus var. gratissimus
• Daphne genkwa
• Daphne holosericea
• Dillenia philippinensis
• Fragaria × ananassa
• Gossypium hirsutum
• Hippophae rhamnoides
• Lamium album
• Magnolia biondii
• Magnolia salicifolia
• Marrubium cylleneum
• Marrubium velutinum
• Phlomoides spectabilis
• Picea obovata
• Potentilla anserina
• Pteridium aquilinum
• Pteridium esculentum
• Quercus ilex
• Quercus laurifolia
• Quercus suber
• Rosa canina
• Rubus chingii
• Rubus corchorifolius
• Solanum crinitum
• Stenochlaena palustris
• Tilia tomentosa
• Tribulus terrestris
• Triumfetta cordifolia
• Waltheria indica

Cross-Links

• PubChem: 57369598
• LOTUS: LTS0145952
• wikiData: Q104990049