8-[(2S,3R,4R,5R,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

Details

• Internal ID: 34e51688-504a-45c6-8fd6-1299fad85a82
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4R,5R,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)C3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]2[C@@H]([C@@H](O[C@H]([C@H]2O)C3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)CO)O)O)O)O
• InChI: InChI=1S/C28H32O14/c1-10-20(33)22(35)23(36)28(39-10)42-27-21(34)17(9-29)41-26(24(27)37)19-14(31)7-13(30)18-15(32)8-16(40-25(18)19)11-3-5-12(38-2)6-4-11/h3-8,10,17,20-24,26-31,33-37H,9H2,1-2H3/t10-,17-,20-,21+,22+,23-,24+,26-,27-,28-/m0/s1
• InChI Key: ROHFXZVXVOFJHV-XEXCBRISSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.75
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6962	69.62%
Caco-2	-	0.8990	89.90%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6357	63.57%
OATP2B1 inhibitior	-	0.7058	70.58%
OATP1B1 inhibitior	+	0.8401	84.01%
OATP1B3 inhibitior	+	0.9154	91.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8191	81.91%
P-glycoprotein inhibitior	-	0.6162	61.62%
P-glycoprotein substrate	-	0.5532	55.32%
CYP3A4 substrate	+	0.6474	64.74%
CYP2C9 substrate	-	0.8555	85.55%
CYP2D6 substrate	-	0.8543	85.43%
CYP3A4 inhibition	-	0.8726	87.26%
CYP2C9 inhibition	-	0.9317	93.17%
CYP2C19 inhibition	-	0.9293	92.93%
CYP2D6 inhibition	-	0.9621	96.21%
CYP1A2 inhibition	-	0.9194	91.94%
CYP2C8 inhibition	+	0.6413	64.13%
CYP inhibitory promiscuity	-	0.7482	74.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7401	74.01%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9301	93.01%
Skin irritation	-	0.8291	82.91%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5099	50.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.6808	68.08%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9233	92.33%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8330	83.30%
Acute Oral Toxicity (c)	III	0.6869	68.69%
Estrogen receptor binding	+	0.8234	82.34%
Androgen receptor binding	+	0.7350	73.50%
Thyroid receptor binding	+	0.5744	57.44%
Glucocorticoid receptor binding	+	0.6269	62.69%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.7453	74.53%
Honey bee toxicity	-	0.7273	72.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7374	73.74%

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	97.52%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.71%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	94.99%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.87%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.12%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.08%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.80%	99.15%
CHEMBL308	P06493	Cyclin-dependent kinase 1	88.93%	91.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.39%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	88.32%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.86%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.92%	81.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.54%	96.09%
CHEMBL4208	P20618	Proteasome component C5	84.50%	90.00%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	84.23%	89.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.67%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.58%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.56%	95.89%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.88%	97.53%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.81%	87.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.44%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	80.00%	93.31%

Plants that contains it

• Anthurium versicolor

Cross-Links

• PubChem: 162870461
• LOTUS: LTS0174935
• wikiData: Q105242221