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

Details

• Internal ID: eb9483f7-a822-49f6-bb4d-9ae8691ff0e7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=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)OC(=O)C5=CC(=C(C(=C5)O)O)O)O
• InChI: InChI=1S/C28H22O16/c29-11-3-1-9(2-4-11)22-23(19(35)17-13(31)7-12(30)8-16(17)41-22)43-28-25(21(37)20(36)24(44-28)26(38)39)42-27(40)10-5-14(32)18(34)15(33)6-10/h1-8,20-21,24-25,28-34,36-37H,(H,38,39)/t20-,21-,24-,25+,28+/m0/s1
• InChI Key: OYBKGCKIYYHOJN-DTCGYDHASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₁₆
• Molecular Weight: 614.50 g/mol
• Exact Mass: 614.09078461 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.9094	90.94%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	+	0.5891	58.91%
OATP1B1 inhibitior	+	0.7305	73.05%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7199	71.99%
P-glycoprotein inhibitior	+	0.7013	70.13%
P-glycoprotein substrate	-	0.5984	59.84%
CYP3A4 substrate	+	0.6607	66.07%
CYP2C9 substrate	-	0.8147	81.47%
CYP2D6 substrate	-	0.8772	87.72%
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	+	0.9450	94.50%
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	-	0.8358	83.58%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7769	77.69%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5657	56.57%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9496	94.96%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.7530	75.30%
Androgen receptor binding	+	0.8083	80.83%
Thyroid receptor binding	+	0.5432	54.32%
Glucocorticoid receptor binding	+	0.5960	59.60%
Aromatase binding	-	0.6128	61.28%
PPAR gamma	+	0.7163	71.63%
Honey bee toxicity	-	0.7898	78.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9599	95.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	99.73%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	99.70%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.12%	91.11%
CHEMBL3194	P02766	Transthyretin	98.58%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.69%	89.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	94.91%	97.53%
CHEMBL2581	P07339	Cathepsin D	94.13%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.61%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.79%	83.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.03%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.00%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.79%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.41%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.39%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	86.03%	94.73%
CHEMBL4530	P00488	Coagulation factor XIII	85.51%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.41%	99.15%
CHEMBL4208	P20618	Proteasome component C5	82.11%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.63%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.55%	91.71%

Plants that contains it

• Melaleuca squarrosa

Cross-Links

• PubChem: 102033017
• LOTUS: LTS0142652
• wikiData: Q105203099