(2S,3S,4R,5S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: bfbcb097-5873-4cf0-8088-8d3bfc873f2e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: (2S,3S,4R,5S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@H]([C@@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15+,16+,19+,21-/m1/s1
• InChI Key: DUBCCGAQYVUYEU-VFKUPZNOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₁₃
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.07474062 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.45
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.9063	90.63%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	+	0.5976	59.76%
OATP1B1 inhibitior	+	0.9400	94.00%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6936	69.36%
P-glycoprotein inhibitior	-	0.5878	58.78%
P-glycoprotein substrate	-	0.8524	85.24%
CYP3A4 substrate	+	0.6157	61.57%
CYP2C9 substrate	-	0.8166	81.66%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.7354	73.54%
CYP2C9 inhibition	-	0.7205	72.05%
CYP2C19 inhibition	-	0.8328	83.28%
CYP2D6 inhibition	-	0.9625	96.25%
CYP1A2 inhibition	-	0.7704	77.04%
CYP2C8 inhibition	+	0.9506	95.06%
CYP inhibitory promiscuity	-	0.8051	80.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6914	69.14%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.7522	75.22%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4868	48.68%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.5343	53.43%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8471	84.71%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.6466	64.66%
Androgen receptor binding	+	0.7800	78.00%
Thyroid receptor binding	-	0.5954	59.54%
Glucocorticoid receptor binding	+	0.5990	59.90%
Aromatase binding	-	0.6169	61.69%
PPAR gamma	+	0.5777	57.77%
Honey bee toxicity	-	0.7860	78.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9599	95.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5573	P09923	Intestinal alkaline phosphatase	891 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.20%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.65%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.48%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.19%	95.64%
CHEMBL3194	P02766	Transthyretin	95.03%	90.71%
CHEMBL2581	P07339	Cathepsin D	93.20%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.90%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.55%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.68%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.43%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.42%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.30%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.71%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.61%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.14%	90.71%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	82.33%	97.53%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.84%	94.00%
CHEMBL4530	P00488	Coagulation factor XIII	80.17%	96.00%

Plants that contains it

• Campanula glomerata
• Fuchsia fulgens
• Hypericum perforatum
• Persicaria hydropiper
• Psidium guajava
• Salvia blepharophylla
• Theobroma grandiflorum

Cross-Links

• PubChem: 154497005
• LOTUS: LTS0221249
• wikiData: Q104989147