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

Details

• Internal ID: 657e7c96-1978-45f6-b59d-17a2e3c629a9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dihydroxy-5-methoxyphenyl)-5-hydroxy-3-methoxy-7-[[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)OCC4C(C(C(C(O4)O)O)O)O)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)OC[C@@H]4[C@H]([C@@H]([C@H](C(O4)O)O)O)O)O)OC
• InChI: InChI=1S/C23H24O13/c1-32-13-4-8(3-11(25)16(13)26)21-22(33-2)18(28)15-10(24)5-9(6-12(15)35-21)34-7-14-17(27)19(29)20(30)23(31)36-14/h3-6,14,17,19-20,23-27,29-31H,7H2,1-2H3/t14-,17-,19+,20-,23?/m1/s1
• InChI Key: FKEXRGAGSYDVCS-BZMFKJDCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₃
• Molecular Weight: 508.40 g/mol
• Exact Mass: 508.12169082 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8656	86.56%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.5627	56.27%
OATP1B1 inhibitior	+	0.8492	84.92%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4670	46.70%
P-glycoprotein inhibitior	-	0.4805	48.05%
P-glycoprotein substrate	-	0.5842	58.42%
CYP3A4 substrate	+	0.6318	63.18%
CYP2C9 substrate	-	0.6658	66.58%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8000	80.00%
CYP inhibitory promiscuity	-	0.6670	66.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9240	92.40%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	+	0.5936	59.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4276	42.76%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9039	90.39%
Acute Oral Toxicity (c)	III	0.6904	69.04%
Estrogen receptor binding	+	0.8815	88.15%
Androgen receptor binding	+	0.6600	66.00%
Thyroid receptor binding	+	0.5509	55.09%
Glucocorticoid receptor binding	+	0.7025	70.25%
Aromatase binding	+	0.6479	64.79%
PPAR gamma	+	0.7665	76.65%
Honey bee toxicity	-	0.8123	81.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.8477	84.77%

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	99.29%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.47%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.23%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.85%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.68%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.56%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	93.14%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.35%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.30%	99.15%
CHEMBL2581	P07339	Cathepsin D	89.43%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.80%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.35%	97.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.08%	95.64%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.70%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.66%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.85%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.49%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.18%	95.78%
CHEMBL2424	Q04760	Glyoxalase I	82.15%	91.67%
CHEMBL3194	P02766	Transthyretin	82.05%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.78%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.52%	94.42%

Plants that contains it

• Arctotis argentea

Cross-Links

• PubChem: 162816987
• LOTUS: LTS0197418
• wikiData: Q104996570