(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylic acid

Details

• Internal ID: b38fb79e-192a-43ac-9e4b-00d9e8de4201
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylic acid
• SMILES (Canonical): C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)C(=O)O)O)O)O)C4=CC=C(C=C4)O
• SMILES (Isomeric): C1[C@H](OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)C4=CC=C(C=C4)O
• InChI: InChI=1S/C21H20O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)/t13-,16-,17-,18+,19-,21+/m0/s1
• InChI Key: BDCRTIDKZGEVEN-CGXGPNJMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• naringenin-7-o-beta-d-glucuronide
• (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylic acid
• Naringenin 7-O-glucuronide
• Naringenin 7-O-beta-D-glucuronide
• (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(((S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxochroman-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
• Naringenin-7-O-glucuronide
• DTXSID60573866
• HY-N2066
• AKOS040760583
• PD044321
• CS-0018571

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4876	48.76%
Caco-2	-	0.9245	92.45%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6413	64.13%
OATP2B1 inhibitior	-	0.5517	55.17%
OATP1B1 inhibitior	+	0.9482	94.82%
OATP1B3 inhibitior	+	0.9826	98.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6471	64.71%
P-glycoprotein inhibitior	-	0.7082	70.82%
P-glycoprotein substrate	-	0.9256	92.56%
CYP3A4 substrate	+	0.5825	58.25%
CYP2C9 substrate	-	0.8215	82.15%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.7087	70.87%
CYP2C9 inhibition	-	0.6268	62.68%
CYP2C19 inhibition	-	0.8335	83.35%
CYP2D6 inhibition	-	0.9041	90.41%
CYP1A2 inhibition	-	0.8388	83.88%
CYP2C8 inhibition	+	0.6456	64.56%
CYP inhibitory promiscuity	-	0.8476	84.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6381	63.81%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8468	84.68%
Skin irritation	-	0.6985	69.85%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5553	55.53%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	-	0.8157	81.57%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4617	46.17%
Acute Oral Toxicity (c)	II	0.3223	32.23%
Estrogen receptor binding	+	0.7592	75.92%
Androgen receptor binding	+	0.5464	54.64%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5840	58.40%
Aromatase binding	+	0.5261	52.61%
PPAR gamma	+	0.6775	67.75%
Honey bee toxicity	-	0.7739	77.39%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9256	92.56%

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	99.07%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.99%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.98%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.52%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.42%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.46%	99.15%
CHEMBL3194	P02766	Transthyretin	89.29%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.68%	99.23%
CHEMBL4208	P20618	Proteasome component C5	88.51%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.20%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.43%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.87%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.70%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.41%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.21%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.72%	91.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.27%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	80.07%	94.73%

Plants that contains it

• Centaurea urvillei
• Garcinia prainiana

Cross-Links

• PubChem: 15540754
• LOTUS: LTS0122350
• wikiData: Q72493890