6-[(2S,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one

Details

• Internal ID: 76a72906-a638-4156-a2b8-233c5681178e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)OC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-40-14-4-9(2-3-10(14)31)13-5-11(32)18-15(41-13)6-12(33)19(22(18)36)26-25(39)27(21(35)17(8-30)42-26)44-28-24(38)23(37)20(34)16(7-29)43-28/h2-6,16-17,20-21,23-31,33-39H,7-8H2,1H3/t16-,17-,20-,21-,23+,24-,25+,26+,27+,28+/m1/s1
• InChI Key: HGWRKIOMUDWHHZ-WJRKJMBXSA-N
• Popularity: 1 reference 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): 266.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.08
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9197	91.97%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5697	56.97%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6646	66.46%
P-glycoprotein inhibitior	-	0.5642	56.42%
P-glycoprotein substrate	-	0.6079	60.79%
CYP3A4 substrate	+	0.6477	64.77%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7549	75.49%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5229	52.29%
Human Ether-a-go-go-Related Gene inhibition	+	0.6478	64.78%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9097	90.97%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8261	82.61%
Androgen receptor binding	+	0.6896	68.96%
Thyroid receptor binding	-	0.4941	49.41%
Glucocorticoid receptor binding	+	0.5523	55.23%
Aromatase binding	+	0.6141	61.41%
PPAR gamma	+	0.7650	76.50%
Honey bee toxicity	-	0.6919	69.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.66%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.22%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.48%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.85%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.76%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.89%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.74%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.21%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.02%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.25%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.83%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.86%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.40%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.93%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	82.60%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.98%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.75%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.29%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.85%	97.36%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 102352203
• LOTUS: LTS0241292
• wikiData: Q105028016