5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexoxy]chromen-4-one

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	53a729b9-1e84-431b-adcc-3c6a5ef88316
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 3-O-methylated flavonoids
IUPAC Name	5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromen-4-one
SMILES (Canonical)	COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4CC(C(C(C4O)O)O)CO)O
SMILES (Isomeric)	COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@@H]4C[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)O
InChI	InChI=1S/C23H24O11/c1-32-14-4-9(2-3-12(14)26)22-23(20(30)17-13(27)6-11(25)7-15(17)33-22)34-16-5-10(8-24)18(28)21(31)19(16)29/h2-4,6-7,10,16,18-19,21,24-29,31H,5,8H2,1H3/t10-,16-,18-,19+,21+/m1/s1
InChI Key	ACDZACLWASKTRT-VQGUZFFKSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₄O₁₁
Molecular Weight	476.40 g/mol
Exact Mass	476.13186158 g/mol
Topological Polar Surface Area (TPSA)	186.00 Å²
XlogP	1.30
Atomic LogP (AlogP)	0.43
H-Bond Acceptor	11
H-Bond Donor	7
Rotatable Bonds	5

Synonyms

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5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexoxy]chromen-4-one

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7161	71.61%
Caco-2	-	0.8942	89.42%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6039	60.39%
OATP2B1 inhibitior	+	0.5839	58.39%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9754	97.54%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6420	64.20%
P-glycoprotein inhibitior	-	0.5699	56.99%
P-glycoprotein substrate	-	0.5182	51.82%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	0.5865	58.65%
CYP2D6 substrate	-	0.7973	79.73%
CYP3A4 inhibition	-	0.7531	75.31%
CYP2C9 inhibition	-	0.8150	81.50%
CYP2C19 inhibition	-	0.7959	79.59%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.6207	62.07%
CYP2C8 inhibition	+	0.8743	87.43%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7021	70.21%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8523	85.23%
Skin irritation	-	0.8030	80.30%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.6128	61.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4785	47.85%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9196	91.96%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7574	75.74%
Acute Oral Toxicity (c)	III	0.6529	65.29%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	-	0.5835	58.35%
Glucocorticoid receptor binding	+	0.7779	77.79%
Aromatase binding	+	0.6091	60.91%
PPAR gamma	+	0.6945	69.45%
Honey bee toxicity	-	0.8039	80.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	-	0.3712	37.12%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.08%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.81%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.97%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.94%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.25%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.25%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.14%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.31%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.75%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.40%	90.71%
CHEMBL3194	P02766	Transthyretin	84.61%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.74%	86.92%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.69%	96.12%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.78%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.64%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.52%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.80%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.13%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.88%	92.94%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.65%	95.53%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.