2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one

Details

• Internal ID: 18f8d519-9d1c-4afc-895a-5b7356864b2b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: 2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=CC=C1CC2(C(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CC2(C(=O)C3=C(O2)C=C(C=C3O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H22O11/c22-8-14-16(25)17(26)18(27)20(31-14)30-12-5-11(24)6-13-15(12)19(28)21(29,32-13)7-9-1-3-10(23)4-2-9/h1-6,14,16-18,20,22-27,29H,7-8H2/t14-,16-,17+,18-,20-,21?/m0/s1
• InChI Key: KJIWCKSQHHNTTL-QZYWKIOKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5084	50.84%
Caco-2	-	0.9187	91.87%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5808	58.08%
OATP2B1 inhibitior	-	0.5564	55.64%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5728	57.28%
P-glycoprotein inhibitior	-	0.6781	67.81%
P-glycoprotein substrate	-	0.8419	84.19%
CYP3A4 substrate	+	0.6064	60.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.8508	85.08%
CYP2C9 inhibition	-	0.9378	93.78%
CYP2C19 inhibition	-	0.8755	87.55%
CYP2D6 inhibition	-	0.8767	87.67%
CYP1A2 inhibition	-	0.8983	89.83%
CYP2C8 inhibition	+	0.6480	64.80%
CYP inhibitory promiscuity	-	0.8599	85.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5999	59.99%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8612	86.12%
Skin irritation	-	0.7854	78.54%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6617	66.17%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8493	84.93%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6420	64.20%
Acute Oral Toxicity (c)	III	0.5433	54.33%
Estrogen receptor binding	+	0.7366	73.66%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6461	64.61%
Aromatase binding	+	0.6257	62.57%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.6792	67.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7732	77.32%

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	99.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.06%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.05%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.91%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.39%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.82%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.65%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.41%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.23%	95.89%
CHEMBL4208	P20618	Proteasome component C5	85.31%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.11%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.03%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.93%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.82%	99.17%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.73%	90.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.33%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.31%	97.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.47%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	82.84%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.28%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	81.28%	95.93%
CHEMBL3194	P02766	Transthyretin	80.67%	90.71%

Plants that contains it

• Chaenomeles sinensis
• Hovenia trichocarpa
• Medicago truncatula
• Pseudolarix amabilis

Cross-Links

• PubChem: 133554286
• LOTUS: LTS0253360
• wikiData: Q104399260