2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one

Details

• Internal ID: 9dffb53d-3740-4336-ac33-8233e1dd0797
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OCC4C(C(C(C(O4)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OCC4[C@H]([C@H]([C@@H](C(O4)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c22-8-4-11(25)14-12(5-8)32-19(7-1-2-9(23)10(24)3-7)20(16(14)27)31-6-13-15(26)17(28)18(29)21(30)33-13/h1-5,13,15,17-18,21-26,28-30H,6H2/t13?,15-,17-,18+,21?/m1/s1
• InChI Key: FZKBNCDAGYDHTP-OBLZSLNYSA-N
• Popularity: 2 references 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: -0.20
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• CHEBI:191415
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxytetrahydropyran-2-yl]methoxy]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4831	48.31%
Caco-2	-	0.8933	89.33%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6755	67.55%
OATP2B1 inhibitior	+	0.7159	71.59%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.8601	86.01%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5757	57.57%
P-glycoprotein inhibitior	-	0.6509	65.09%
P-glycoprotein substrate	-	0.7775	77.75%
CYP3A4 substrate	+	0.6205	62.05%
CYP2C9 substrate	-	0.6658	66.58%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.8972	89.72%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.9282	92.82%
CYP inhibitory promiscuity	-	0.7389	73.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8334	83.34%
Skin irritation	-	0.7899	78.99%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	+	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4513	45.13%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9130	91.30%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8588	85.88%
Acute Oral Toxicity (c)	III	0.4462	44.62%
Estrogen receptor binding	+	0.6930	69.30%
Androgen receptor binding	+	0.7616	76.16%
Thyroid receptor binding	-	0.5263	52.63%
Glucocorticoid receptor binding	+	0.6653	66.53%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6598	65.98%
Honey bee toxicity	-	0.7271	72.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8944	89.44%

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	99.34%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.94%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.10%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.48%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	91.94%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.88%	95.64%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.39%	99.17%
CHEMBL1929	P47989	Xanthine dehydrogenase	91.30%	96.12%
CHEMBL1951	P21397	Monoamine oxidase A	90.41%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.74%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.41%	95.78%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.85%	80.33%
CHEMBL3194	P02766	Transthyretin	88.42%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.16%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.15%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.82%	86.92%

Plants that contains it

• Daphne genkwa
• Symplocos paniculata

Cross-Links

• PubChem: 5480505
• NPASS: NPC7596