2-(3,4-dihydroxyphenyl)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxychromen-4-one

Details

• Internal ID: 3b1c2704-71de-455e-a720-098cdf16573a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)COC6C(C(C(C(O6)CO)O)O)O)O)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]([C@@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)CO[C@H]6[C@@H]([C@H]([C@@H]([C@@H](O6)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O21/c1-9-19(39)23(43)27(47)32(49-9)54-30-25(45)21(41)17(8-48-31-26(46)24(44)20(40)16(7-34)51-31)52-33(30)53-29-22(42)18-14(38)5-11(35)6-15(18)50-28(29)10-2-3-12(36)13(37)4-10/h2-6,9,16-17,19-21,23-27,30-41,43-47H,7-8H2,1H3/t9-,16+,17+,19+,20-,21+,23+,24+,25+,26-,27+,30+,31-,32+,33+/m1/s1
• InChI Key: NRTALHZHXXNSOY-AEPLQJBTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₂₁
• Molecular Weight: 772.70 g/mol
• Exact Mass: 772.20620828 g/mol
• Topological Polar Surface Area (TPSA): 345.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.86
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5372	53.72%
Caco-2	-	0.9134	91.34%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6684	66.84%
OATP2B1 inhibitior	-	0.7131	71.31%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6276	62.76%
P-glycoprotein inhibitior	-	0.5208	52.08%
P-glycoprotein substrate	+	0.5629	56.29%
CYP3A4 substrate	+	0.6734	67.34%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9252	92.52%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	+	0.8450	84.50%
CYP inhibitory promiscuity	-	0.6991	69.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6759	67.59%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7163	71.63%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.9289	92.89%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8945	89.45%
Acute Oral Toxicity (c)	III	0.5567	55.67%
Estrogen receptor binding	+	0.8335	83.35%
Androgen receptor binding	+	0.5973	59.73%
Thyroid receptor binding	+	0.5262	52.62%
Glucocorticoid receptor binding	-	0.5301	53.01%
Aromatase binding	+	0.5539	55.39%
PPAR gamma	+	0.7345	73.45%
Honey bee toxicity	-	0.7003	70.03%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.8024	80.24%

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	99.71%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.22%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.04%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.27%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.73%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.79%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.41%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.50%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.72%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.14%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.62%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.94%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.75%	86.92%
CHEMBL3194	P02766	Transthyretin	85.56%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.04%	95.64%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.88%	80.78%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.78%	95.78%
CHEMBL4208	P20618	Proteasome component C5	80.36%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.06%	97.09%

Plants that contains it

• Capparis spinosa

Cross-Links

• PubChem: 162976606
• LOTUS: LTS0004089
• wikiData: Q105184799