3-[(2R,3S,4R,5R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 68e8367b-7f0c-4442-9261-95d110544050
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2R,3S,4R,5R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)OC5C(C(CO5)(CO)O)O)C6=CC(=C(C=C6)O)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)O[C@@H]3[C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O)C6=CC(=C(C=C6)O)OC)O
• InChI: InChI=1S/C33H40O20/c1-45-13-6-15(37)20-17(7-13)49-26(12-3-4-14(36)16(5-12)46-2)27(23(20)40)52-31-28(53-32-29(43)33(44,10-35)11-48-32)22(39)19(51-31)9-47-30-25(42)24(41)21(38)18(8-34)50-30/h3-7,18-19,21-22,24-25,28-32,34-39,41-44H,8-11H2,1-2H3/t18-,19-,21-,22-,24+,25-,28+,29+,30-,31-,32+,33-/m1/s1
• InChI Key: KVSUVYZMSXVWNS-YNHUXGOTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₀
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.21129366 g/mol
• Topological Polar Surface Area (TPSA): 302.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -3.00
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6634	66.34%
Caco-2	-	0.8986	89.86%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6223	62.23%
OATP2B1 inhibitior	-	0.7223	72.23%
OATP1B1 inhibitior	+	0.8930	89.30%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7470	74.70%
P-glycoprotein inhibitior	+	0.6140	61.40%
P-glycoprotein substrate	+	0.6048	60.48%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8178	81.78%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.8665	86.65%
CYP2D6 inhibition	-	0.9193	91.93%
CYP1A2 inhibition	-	0.8977	89.77%
CYP2C8 inhibition	+	0.8143	81.43%
CYP inhibitory promiscuity	-	0.7651	76.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.8182	81.82%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	+	0.5472	54.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7329	73.29%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7552	75.52%
Acute Oral Toxicity (c)	III	0.6977	69.77%
Estrogen receptor binding	+	0.8344	83.44%
Androgen receptor binding	+	0.6458	64.58%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6281	62.81%
Aromatase binding	+	0.6294	62.94%
PPAR gamma	+	0.7278	72.78%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7109	71.09%

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%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.19%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.46%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.26%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.81%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.10%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.59%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.29%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.41%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	92.39%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.94%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.18%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.19%	97.36%
CHEMBL4208	P20618	Proteasome component C5	87.81%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.66%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.91%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.89%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.09%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.84%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.67%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.51%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.48%	95.53%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.06%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	84.60%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	82.53%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.05%	92.62%
CHEMBL4581	P52732	Kinesin-like protein 1	81.03%	93.18%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.82%	97.28%

Plants that contains it

• Retama sphaerocarpa

Cross-Links

• PubChem: 10533135
• LOTUS: LTS0167355
• wikiData: Q105146703