3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one

Details

• Internal ID: 0987cbe1-cd7f-4dda-ae04-9e6c8289d61f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
• InChI: InChI=1S/C28H32O16/c1-9-18(31)22(35)24(37)27(41-9)40-8-16-20(33)23(36)28(43-16)44-26-21(34)17-12(30)6-11(29)7-13(17)42-25(26)10-4-14(38-2)19(32)15(5-10)39-3/h4-7,9,16,18,20,22-24,27-33,35-37H,8H2,1-3H3/t9-,16-,18-,20-,22+,23+,24+,27+,28-/m0/s1
• InChI Key: DUDOAFBUHCTQHF-GILAHISDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₆
• Molecular Weight: 624.50 g/mol
• Exact Mass: 624.16903493 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6626	66.26%
Caco-2	-	0.9020	90.20%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7402	74.02%
OATP2B1 inhibitior	-	0.7188	71.88%
OATP1B1 inhibitior	+	0.8476	84.76%
OATP1B3 inhibitior	+	0.9134	91.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5675	56.75%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.6569	65.69%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.8267	82.67%
CYP2C9 inhibition	-	0.8099	80.99%
CYP2C19 inhibition	-	0.7969	79.69%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.8073	80.73%
CYP inhibitory promiscuity	+	0.5296	52.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5847	58.47%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9030	90.30%
Skin irritation	-	0.8356	83.56%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4335	43.35%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9134	91.34%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9035	90.35%
Acute Oral Toxicity (c)	III	0.7031	70.31%
Estrogen receptor binding	+	0.8433	84.33%
Androgen receptor binding	+	0.5604	56.04%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.6763	67.63%
Aromatase binding	+	0.5951	59.51%
PPAR gamma	+	0.7314	73.14%
Honey bee toxicity	-	0.7662	76.62%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8887	88.87%

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	99.44%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.65%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.40%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.94%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.27%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	91.40%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.11%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.02%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.58%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL3194	P02766	Transthyretin	86.44%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.47%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.84%	95.89%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.78%	94.03%
CHEMBL4208	P20618	Proteasome component C5	82.28%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.98%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	81.62%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.10%	92.94%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.04%	94.42%

Plants that contains it

• Lysimachia congestiflora

Cross-Links

• PubChem: 102438663
• LOTUS: LTS0057685
• wikiData: Q104989177