2-[(alphaZ)-3,4-Dihydroxybenzylidene]-6-(3-O,4-O,6-O-triacetyl-beta-D-glucopyranosyloxy)-7-hydroxybenzofuran-3(2H)-one

Details

• Internal ID: 68a1a2d2-ff66-4147-8bd1-966df572356b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-6-[[(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy]-5-hydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=C(C3=C(C=C2)C(=O)C(=CC4=CC(=C(C=C4)O)O)O3)O)O)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(C3=C(C=C2)C(=O)/C(=C/C4=CC(=C(C=C4)O)O)/O3)O)O)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H26O14/c1-11(28)36-10-20-25(37-12(2)29)26(38-13(3)30)23(35)27(41-20)40-18-7-5-15-21(33)19(39-24(15)22(18)34)9-14-4-6-16(31)17(32)8-14/h4-9,20,23,25-27,31-32,34-35H,10H2,1-3H3/b19-9-/t20-,23-,25-,26-,27-/m1/s1
• InChI Key: AHLQXSOCSBYAFH-LVNWGQRMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₄
• Molecular Weight: 574.50 g/mol
• Exact Mass: 574.13225550 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9512	95.12%
Caco-2	-	0.8656	86.56%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8158	81.58%
OATP2B1 inhibitior	-	0.5731	57.31%
OATP1B1 inhibitior	+	0.8504	85.04%
OATP1B3 inhibitior	+	0.8197	81.97%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8426	84.26%
P-glycoprotein inhibitior	+	0.7958	79.58%
P-glycoprotein substrate	-	0.7117	71.17%
CYP3A4 substrate	+	0.6577	65.77%
CYP2C9 substrate	-	0.8059	80.59%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.8535	85.35%
CYP2C9 inhibition	-	0.6783	67.83%
CYP2C19 inhibition	-	0.5280	52.80%
CYP2D6 inhibition	-	0.8941	89.41%
CYP1A2 inhibition	-	0.5711	57.11%
CYP2C8 inhibition	+	0.6619	66.19%
CYP inhibitory promiscuity	-	0.5713	57.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5953	59.53%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8814	88.14%
Skin irritation	-	0.7935	79.35%
Skin corrosion	-	0.9522	95.22%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7511	75.11%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8223	82.23%
Acute Oral Toxicity (c)	III	0.6109	61.09%
Estrogen receptor binding	+	0.7505	75.05%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.5236	52.36%
Glucocorticoid receptor binding	+	0.6836	68.36%
Aromatase binding	-	0.5278	52.78%
PPAR gamma	+	0.6905	69.05%
Honey bee toxicity	-	0.7239	72.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.99%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.55%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.75%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.64%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.81%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.06%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.06%	95.56%
CHEMBL3194	P02766	Transthyretin	88.67%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.75%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.19%	83.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.57%	96.00%
CHEMBL4208	P20618	Proteasome component C5	85.03%	90.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.36%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.31%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.08%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.02%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.99%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.75%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.88%	80.78%
CHEMBL340	P08684	Cytochrome P450 3A4	81.64%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.61%	96.90%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Calea lantanoides
• Chromolaena odorata
• Cibotium barometz
• Coronilla cretica
• Drosera indica
• Drummondita hassellii
• Ephedra distachya
• Flindersia xanthoxyla
• Galium mollugo
• Gardenia imperialis
• Gomesa radicans
• Grindelia scorzonerifolia
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Pinus flexilis
• Psilotum nudum
• Rydingia limbata
• Senegalia mellifera
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 10603216
• NPASS: NPC288506
• LOTUS: LTS0107725
• wikiData: Q104912317