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

Details

• Internal ID: f1c55677-a917-4763-8e65-a088c32a4f1f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)C(=O)O)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC(=C(C=C4)O)O)O)C(=O)O)O)O
• InChI: InChI=1S/C23H20O13/c1-8(24)33-21-19(30)18(29)20(22(31)32)36-23(21)34-10-5-13(27)17-14(28)7-15(35-16(17)6-10)9-2-3-11(25)12(26)4-9/h2-7,18-21,23,25-27,29-30H,1H3,(H,31,32)/t18-,19-,20-,21+,23+/m0/s1
• InChI Key: CLHBTRPTHKBXEO-YKZCJQPKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₁₃
• Molecular Weight: 504.40 g/mol
• Exact Mass: 504.09039069 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7495	74.95%
Caco-2	-	0.9060	90.60%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7171	71.71%
OATP2B1 inhibitior	-	0.5365	53.65%
OATP1B1 inhibitior	+	0.9464	94.64%
OATP1B3 inhibitior	+	0.9745	97.45%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7778	77.78%
P-glycoprotein inhibitior	-	0.5240	52.40%
P-glycoprotein substrate	-	0.7800	78.00%
CYP3A4 substrate	+	0.6206	62.06%
CYP2C9 substrate	+	0.5402	54.02%
CYP2D6 substrate	-	0.8791	87.91%
CYP3A4 inhibition	-	0.8307	83.07%
CYP2C9 inhibition	-	0.8102	81.02%
CYP2C19 inhibition	-	0.8717	87.17%
CYP2D6 inhibition	-	0.9680	96.80%
CYP1A2 inhibition	-	0.6999	69.99%
CYP2C8 inhibition	+	0.7928	79.28%
CYP inhibitory promiscuity	-	0.7743	77.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.6672	66.72%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	-	0.5064	50.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4038	40.38%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6907	69.07%
skin sensitisation	-	0.9127	91.27%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8850	88.50%
Acute Oral Toxicity (c)	III	0.5185	51.85%
Estrogen receptor binding	+	0.7802	78.02%
Androgen receptor binding	+	0.7537	75.37%
Thyroid receptor binding	-	0.5122	51.22%
Glucocorticoid receptor binding	+	0.6559	65.59%
Aromatase binding	-	0.6143	61.43%
PPAR gamma	+	0.6535	65.35%
Honey bee toxicity	-	0.6987	69.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9611	96.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.86%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.81%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.52%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.44%	99.15%
CHEMBL3194	P02766	Transthyretin	94.19%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.46%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.31%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.14%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.81%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.67%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.21%	85.14%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.15%	95.64%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.14%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.54%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.21%	91.19%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	83.62%	97.53%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.44%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.05%	83.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.98%	81.11%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.94%	89.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.56%	95.89%

Plants that contains it

• Eschscholzia californica
• Inulanthera nuda

Cross-Links

• PubChem: 100924966
• NPASS: NPC297696
• LOTUS: LTS0176927
• wikiData: Q104667522