3-[(2S,3R,4S,5R,6S)-6-[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3-oxopropanoic acid

Details

• Internal ID: f6e4938e-cbd3-4ead-b48c-5706982483fb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6S)-6-[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3-oxopropanoic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)OC)O)O)O)OC(=O)CC(=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)OC)O)O)O)OC(=O)CC(=O)O
• InChI: InChI=1S/C25H24O15/c1-8-21(39-16(32)7-15(30)31)19(34)20(35)25(37-8)40-24-18(33)17-11(27)5-10(26)6-14(17)38-22(24)9-3-12(28)23(36-2)13(29)4-9/h3-6,8,19-21,25-29,34-35H,7H2,1-2H3,(H,30,31)/t8-,19-,20+,21-,25-/m0/s1
• InChI Key: ZYSQXSNEDGAKCG-ZQBNUUHHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₁₅
• Molecular Weight: 564.40 g/mol
• Exact Mass: 564.11152005 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6970	69.70%
Caco-2	-	0.8615	86.15%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5889	58.89%
OATP2B1 inhibitior	-	0.5636	56.36%
OATP1B1 inhibitior	+	0.8598	85.98%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4773	47.73%
P-glycoprotein inhibitior	+	0.6744	67.44%
P-glycoprotein substrate	+	0.6042	60.42%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	+	0.5371	53.71%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.7873	78.73%
CYP2C9 inhibition	-	0.9413	94.13%
CYP2C19 inhibition	-	0.9546	95.46%
CYP2D6 inhibition	-	0.9034	90.34%
CYP1A2 inhibition	-	0.9486	94.86%
CYP2C8 inhibition	+	0.7630	76.30%
CYP inhibitory promiscuity	-	0.8748	87.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6245	62.45%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.7916	79.16%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4505	45.05%
Micronuclear	+	0.8418	84.18%
Hepatotoxicity	-	0.5322	53.22%
skin sensitisation	-	0.9257	92.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8928	89.28%
Acute Oral Toxicity (c)	III	0.6189	61.89%
Estrogen receptor binding	+	0.8005	80.05%
Androgen receptor binding	+	0.5893	58.93%
Thyroid receptor binding	+	0.5656	56.56%
Glucocorticoid receptor binding	+	0.7229	72.29%
Aromatase binding	+	0.5287	52.87%
PPAR gamma	+	0.6882	68.82%
Honey bee toxicity	-	0.8154	81.54%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8442	84.42%

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	99.41%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.07%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.03%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.68%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.94%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.67%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.14%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.77%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.99%	94.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.54%	81.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.12%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	85.11%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.86%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.78%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.44%	95.56%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.10%	94.42%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.01%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.80%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	81.63%	91.19%
CHEMBL4208	P20618	Proteasome component C5	81.38%	90.00%
CHEMBL4530	P00488	Coagulation factor XIII	80.20%	96.00%

Plants that contains it

• Ribes alpinum

Cross-Links

• PubChem: 101720809
• LOTUS: LTS0164345
• wikiData: Q105386394