3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: f12a5da6-04c8-4ff1-a39a-00691b2bf982
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O)C6=CC=C(C=C6)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)C6=CC=C(C=C6)O)O)O)O)O
• InChI: InChI=1S/C32H38O19/c1-10-19(37)23(41)26(44)31(46-10)47-13-6-14(35)18-16(7-13)48-27(11-2-4-12(34)5-3-11)28(22(18)40)50-32-29(24(42)21(39)17(8-33)49-32)51-30-25(43)20(38)15(36)9-45-30/h2-7,10,15,17,19-21,23-26,29-39,41-44H,8-9H2,1H3/t10-,15+,17+,19-,20-,21-,23+,24-,25+,26+,29+,30-,31-,32-/m0/s1
• InChI Key: DXIHKRRIIAWHMF-NEIMAXPJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₉
• Molecular Weight: 726.60 g/mol
• Exact Mass: 726.20072898 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -3.28
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4670	46.70%
Caco-2	-	0.9159	91.59%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5874	58.74%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8739	87.39%
P-glycoprotein inhibitior	-	0.4731	47.31%
P-glycoprotein substrate	+	0.5960	59.60%
CYP3A4 substrate	+	0.6824	68.24%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9515	95.15%
CYP2C9 inhibition	-	0.9608	96.08%
CYP2C19 inhibition	-	0.9462	94.62%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9105	91.05%
CYP2C8 inhibition	+	0.7446	74.46%
CYP inhibitory promiscuity	-	0.8508	85.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6795	67.95%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.8303	83.03%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5563	55.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7650	76.50%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9236	92.36%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9541	95.41%
Acute Oral Toxicity (c)	III	0.6207	62.07%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.5779	57.79%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5256	52.56%
Aromatase binding	+	0.5369	53.69%
PPAR gamma	+	0.7427	74.27%
Honey bee toxicity	-	0.7046	70.46%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.7336	73.36%

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	99.67%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.47%	91.49%
CHEMBL2581	P07339	Cathepsin D	98.17%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.55%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.53%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.64%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.52%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.47%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.41%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	90.81%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.94%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.96%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.28%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.46%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.41%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.34%	95.78%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.14%	95.83%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.05%	93.10%
CHEMBL4208	P20618	Proteasome component C5	84.74%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.40%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.03%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.17%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.12%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.26%	80.33%

Plants that contains it

• Rhodiola rosea

Cross-Links

• PubChem: 162855253
• LOTUS: LTS0256113
• wikiData: Q104991015