3-[5-(1,2-Dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Details

• Internal ID: 9e8cbcd7-047f-44a8-814e-5800945110ff
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(O4)C(CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(O4)C(CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2
• InChI Key: OPJZLUXFQFQYAI-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• 3-[5-(1,2-Dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• DTXSID50871989
• BCP11535
• Isotrifolin;Quercetin 3-O-beta-D-glucofuranoside
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl hexofuranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6907	69.07%
Caco-2	-	0.9132	91.32%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6366	63.66%
OATP2B1 inhibitior	+	0.5944	59.44%
OATP1B1 inhibitior	+	0.9302	93.02%
OATP1B3 inhibitior	+	0.9023	90.23%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5597	55.97%
P-glycoprotein inhibitior	-	0.5954	59.54%
P-glycoprotein substrate	-	0.6652	66.52%
CYP3A4 substrate	+	0.6430	64.30%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.7521	75.21%
CYP2C9 inhibition	-	0.8969	89.69%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.8355	83.55%
CYP1A2 inhibition	-	0.8729	87.29%
CYP2C8 inhibition	+	0.8808	88.08%
CYP inhibitory promiscuity	-	0.6453	64.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6205	62.05%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7549	75.49%
Skin irritation	-	0.7918	79.18%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5566	55.66%
Micronuclear	+	0.6833	68.33%
Hepatotoxicity	-	0.5821	58.21%
skin sensitisation	-	0.8682	86.82%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7948	79.48%
Acute Oral Toxicity (c)	III	0.5569	55.69%
Estrogen receptor binding	+	0.6928	69.28%
Androgen receptor binding	+	0.7880	78.80%
Thyroid receptor binding	+	0.5232	52.32%
Glucocorticoid receptor binding	+	0.6688	66.88%
Aromatase binding	+	0.5385	53.85%
PPAR gamma	+	0.6333	63.33%
Honey bee toxicity	-	0.7623	76.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8004	80.04%

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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.12%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.75%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.32%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.60%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.26%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.20%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.01%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.98%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.61%	96.12%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.62%	90.71%
CHEMBL3194	P02766	Transthyretin	86.55%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.23%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.34%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.11%	94.00%
CHEMBL1900	P15121	Aldose reductase	84.30%	92.38%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.91%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.17%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.20%	97.09%
CHEMBL4208	P20618	Proteasome component C5	80.89%	90.00%

Plants that contains it

• Acmella ciliata
• Astragalus bornmuellerianus
• Astragalus captiosus
• Camellia japonica
• Camellia sinensis
• Caragana spinosa
• Euphorbia smirnovii
• Globularia bisnagarica
• Hypericum brasiliense
• Hypericum elegans
• Hypericum perforatum
• Lagerstroemia speciosa
• Marrubium velutinum
• Nelumbo nucifera
• Phaseolus vulgaris
• Phoenix loureiroi var. loureiroi
• Phyllanthus virgatus
• Potentilla anserina
• Salix caprea
• Salix denticulata
• Sorbus aria
• Tripodanthus acutifolius
• Viburnum tinus
• Vicia sativa
• Volutaria lippii subsp. lippii
• Warburgia ugandensis

Cross-Links

• PubChem: 13179952
• LOTUS: LTS0258961
• wikiData: Q105196399