3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 16adf317-fb28-4b7c-968f-2c5a3bb57b1e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-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)COC6C(C(C(CO6)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)CO[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C32H38O19/c1-10-19(37)23(41)26(44)31(47-10)51-29-24(42)21(39)17(9-46-30-25(43)20(38)15(36)8-45-30)49-32(29)50-28-22(40)18-14(35)6-13(34)7-16(18)48-27(28)11-2-4-12(33)5-3-11/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: UOUUHUNWVKKMRL-RWPOIHIKSA-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: -2.50
• Atomic LogP (AlogP): -2.93
• 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	+	0.5925	59.25%
Caco-2	-	0.9178	91.78%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7137	71.37%
OATP2B1 inhibitior	-	0.7149	71.49%
OATP1B1 inhibitior	+	0.8733	87.33%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7863	78.63%
P-glycoprotein inhibitior	-	0.5777	57.77%
P-glycoprotein substrate	+	0.6772	67.72%
CYP3A4 substrate	+	0.6881	68.81%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.9488	94.88%
CYP2C9 inhibition	-	0.9543	95.43%
CYP2C19 inhibition	-	0.9153	91.53%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.8945	89.45%
CYP2C8 inhibition	+	0.7998	79.98%
CYP inhibitory promiscuity	-	0.8711	87.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6792	67.92%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9110	91.10%
Skin irritation	-	0.8344	83.44%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7246	72.46%
Micronuclear	+	0.5874	58.74%
Hepatotoxicity	-	0.5851	58.51%
skin sensitisation	-	0.9166	91.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9687	96.87%
Acute Oral Toxicity (c)	III	0.5957	59.57%
Estrogen receptor binding	+	0.8458	84.58%
Androgen receptor binding	+	0.6126	61.26%
Thyroid receptor binding	+	0.5386	53.86%
Glucocorticoid receptor binding	-	0.4860	48.60%
Aromatase binding	+	0.5548	55.48%
PPAR gamma	+	0.7352	73.52%
Honey bee toxicity	-	0.7252	72.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9007	90.07%

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	99.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.03%	91.49%
CHEMBL2581	P07339	Cathepsin D	98.22%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.07%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.15%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.47%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.92%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.16%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.74%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.25%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	86.38%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.65%	97.09%
CHEMBL4208	P20618	Proteasome component C5	85.33%	90.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.48%	80.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.33%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.92%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.79%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.65%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.59%	93.10%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.36%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	80.79%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.22%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.12%	95.89%

Plants that contains it

• Primula hirsuta

Cross-Links

• PubChem: 102321609
• LOTUS: LTS0232283
• wikiData: Q105276580