3-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Details

• Internal ID: 1793df58-f703-477f-bdd2-4070ec397773
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)OC5C(C(C(CO5)O)O)O)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)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O
• InChI: InChI=1S/C26H28O16/c1-7-16(32)20(36)24(42-25-21(37)18(34)13(31)6-38-25)26(39-7)41-23-19(35)15-10(28)4-9(27)5-14(15)40-22(23)8-2-11(29)17(33)12(30)3-8/h2-5,7,13,16,18,20-21,24-34,36-37H,6H2,1H3/t7-,13+,16-,18-,20+,21+,24+,25-,26+/m0/s1
• InChI Key: SMSLFVKERUHQMM-NADTVUILSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₆
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.13773480 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.34
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7160	71.60%
Caco-2	-	0.9027	90.27%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6720	67.20%
OATP2B1 inhibitior	-	0.5614	56.14%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.8917	89.17%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7096	70.96%
P-glycoprotein inhibitior	-	0.5685	56.85%
P-glycoprotein substrate	+	0.6023	60.23%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9278	92.78%
CYP2C9 inhibition	-	0.9538	95.38%
CYP2C19 inhibition	-	0.9355	93.55%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.8650	86.50%
CYP2C8 inhibition	+	0.7428	74.28%
CYP inhibitory promiscuity	-	0.8976	89.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6476	64.76%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8946	89.46%
Skin irritation	-	0.7836	78.36%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4063	40.63%
Micronuclear	+	0.7433	74.33%
Hepatotoxicity	-	0.5519	55.19%
skin sensitisation	-	0.9187	91.87%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9501	95.01%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.8050	80.50%
Androgen receptor binding	+	0.6416	64.16%
Thyroid receptor binding	+	0.6079	60.79%
Glucocorticoid receptor binding	+	0.6903	69.03%
Aromatase binding	+	0.5418	54.18%
PPAR gamma	+	0.7380	73.80%
Honey bee toxicity	-	0.7775	77.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.8557	85.57%

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	99.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.20%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.48%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.12%	95.64%
CHEMBL2581	P07339	Cathepsin D	95.68%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.26%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.34%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.74%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.15%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.78%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.65%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.26%	96.09%
CHEMBL4208	P20618	Proteasome component C5	86.45%	90.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.30%	94.42%
CHEMBL3194	P02766	Transthyretin	85.01%	90.71%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.90%	80.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.46%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.62%	91.38%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.40%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.39%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.69%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.11%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.37%	100.00%

Plants that contains it

• Moquilea pyrifolia

Cross-Links

• PubChem: 162926218
• LOTUS: LTS0138324
• wikiData: Q105256146