6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: b4e04bc6-6e67-4d80-930f-22d93a0e774f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: 6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O
• InChI: InChI=1S/C22H20O13/c1-32-11-4-7(2-3-9(11)24)18-19(14(26)13-10(25)5-8(23)6-12(13)33-18)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-25,27-29H,1H3,(H,30,31)
• InChI Key: VVZWHOMBDMMRSC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₃
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.09039069 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.14
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• CHEBI:182425
• 6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• NCGC00385981-01!6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7483	74.83%
Caco-2	-	0.8931	89.31%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	+	0.5909	59.09%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5280	52.80%
P-glycoprotein inhibitior	-	0.5364	53.64%
P-glycoprotein substrate	-	0.7621	76.21%
CYP3A4 substrate	+	0.6305	63.05%
CYP2C9 substrate	-	0.8245	82.45%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.7674	76.74%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.8511	85.11%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.6411	64.11%
CYP2C8 inhibition	+	0.9339	93.39%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8357	83.57%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5362	53.62%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6407	64.07%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8404	84.04%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.7336	73.36%
Androgen receptor binding	+	0.7125	71.25%
Thyroid receptor binding	-	0.5991	59.91%
Glucocorticoid receptor binding	+	0.7388	73.88%
Aromatase binding	-	0.5994	59.94%
PPAR gamma	+	0.5802	58.02%
Honey bee toxicity	-	0.8192	81.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9235	92.35%

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	98.17%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.25%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.73%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.30%	95.56%
CHEMBL3194	P02766	Transthyretin	93.55%	90.71%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.32%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.40%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.26%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.34%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	87.51%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.32%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.10%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.97%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.43%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.29%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.63%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.64%	95.78%
CHEMBL4208	P20618	Proteasome component C5	80.83%	90.00%

Plants that contains it

• Arachis hypogaea
• Bellis perennis
• Coleogyne ramosissima
• Persicaria hydropiper

Cross-Links

• PubChem: 45782983
• LOTUS: LTS0159542
• wikiData: Q105297967