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

Details

• Internal ID: 8b37ff9a-cc2c-49aa-bb81-5a44bd09c3fa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6S)-6-[2-(3,4-dihydroxy-5-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)OC)O)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)OC)O)O)O)O)OC(=O)CC(=O)O
• InChI: InChI=1S/C25H24O15/c1-8-22(39-16(31)7-15(29)30)20(34)21(35)25(37-8)40-24-19(33)17-11(27)5-10(26)6-13(17)38-23(24)9-3-12(28)18(32)14(4-9)36-2/h3-6,8,20-22,25-28,32,34-35H,7H2,1-2H3,(H,29,30)/t8-,20-,21-,22-,25-/m0/s1
• InChI Key: CLJHAXXQLXXEAX-TZUKPBLKSA-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	-	0.8658	86.58%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5889	58.89%
OATP2B1 inhibitior	-	0.5632	56.32%
OATP1B1 inhibitior	+	0.8475	84.75%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5759	57.59%
P-glycoprotein inhibitior	+	0.6391	63.91%
P-glycoprotein substrate	+	0.6909	69.09%
CYP3A4 substrate	+	0.6558	65.58%
CYP2C9 substrate	-	0.6355	63.55%
CYP2D6 substrate	-	0.8682	86.82%
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	+	0.8483	84.83%
CYP inhibitory promiscuity	-	0.8748	87.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6245	62.45%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8954	89.54%
Skin irritation	-	0.7916	79.16%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4592	45.92%
Micronuclear	+	0.8418	84.18%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9257	92.57%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9052	90.52%
Acute Oral Toxicity (c)	III	0.6189	61.89%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.6491	64.91%
Thyroid receptor binding	+	0.5244	52.44%
Glucocorticoid receptor binding	+	0.7455	74.55%
Aromatase binding	+	0.5362	53.62%
PPAR gamma	+	0.7142	71.42%
Honey bee toxicity	-	0.8062	80.62%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5949	59.49%
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	99.52%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.20%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.75%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.06%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.96%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.92%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.20%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.13%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.42%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.25%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.67%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	86.65%	90.20%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.52%	94.42%
CHEMBL3194	P02766	Transthyretin	85.94%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.58%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.36%	94.73%
CHEMBL2424	Q04760	Glyoxalase I	83.98%	91.67%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.96%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.59%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.99%	90.71%
CHEMBL4530	P00488	Coagulation factor XIII	82.96%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.62%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.74%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.23%	92.62%

Plants that contains it

• Ribes alpinum

Cross-Links

• PubChem: 163103682
• LOTUS: LTS0058208
• wikiData: Q104963499