8-[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: 0d31c2ea-18c1-4fae-9f67-c363a4c53f1a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 8-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1C(C(C(O1)C2=C3C(=C(C(=C2O)C4C(C(C(C(O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)(CO)O
• SMILES (Isomeric): C1C(C(C(O1)C2=C3C(=C(C(=C2O)C4C(C(C(C(O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)(CO)O
• InChI: InChI=1S/C26H28O14/c27-6-13-17(31)20(34)21(35)23(40-13)15-18(32)14-11(30)5-12(9-1-3-10(29)4-2-9)39-22(14)16(19(15)33)24-25(36)26(37,7-28)8-38-24/h1-5,13,17,20-21,23-25,27-29,31-37H,6-8H2
• InChI Key: VZBJDZWPLLGMPG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8026	80.26%
Caco-2	-	0.9135	91.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6083	60.83%
OATP2B1 inhibitior	-	0.5598	55.98%
OATP1B1 inhibitior	+	0.8347	83.47%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7505	75.05%
P-glycoprotein inhibitior	-	0.5165	51.65%
P-glycoprotein substrate	-	0.6240	62.40%
CYP3A4 substrate	+	0.6543	65.43%
CYP2C9 substrate	-	0.6173	61.73%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.8349	83.49%
CYP2C9 inhibition	-	0.9035	90.35%
CYP2C19 inhibition	-	0.8577	85.77%
CYP2D6 inhibition	-	0.9000	90.00%
CYP1A2 inhibition	-	0.8783	87.83%
CYP2C8 inhibition	+	0.6834	68.34%
CYP inhibitory promiscuity	-	0.8317	83.17%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5507	55.07%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.8894	88.94%
Skin irritation	-	0.7872	78.72%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	+	0.6566	65.66%
Human Ether-a-go-go-Related Gene inhibition	-	0.3718	37.18%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8426	84.26%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7382	73.82%
Acute Oral Toxicity (c)	III	0.5050	50.50%
Estrogen receptor binding	+	0.7819	78.19%
Androgen receptor binding	+	0.7544	75.44%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6189	61.89%
Aromatase binding	+	0.6894	68.94%
PPAR gamma	+	0.7504	75.04%
Honey bee toxicity	-	0.7143	71.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.6415	64.15%

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	99.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.31%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.53%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.12%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.35%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	91.82%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	90.69%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.62%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.36%	99.15%
CHEMBL242	Q92731	Estrogen receptor beta	84.99%	98.35%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	84.88%	96.69%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.59%	86.92%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.31%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.25%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.82%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.09%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.44%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.16%	100.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.09%	85.11%

Plants that contains it

• Sicyos edulis
• Sonchus asper
• Xanthosoma sagittifolium

Cross-Links

• PubChem: 74977461
• LOTUS: LTS0138552
• wikiData: Q105385106