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

Details

• Internal ID: 650ccb1b-d9de-467d-b693-32b7cd8681fe
• 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-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(CO5)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)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
• InChI: InChI=1S/C27H30O15/c1-37-12-4-2-10(3-5-12)23-24(20(34)17-13(30)6-11(29)7-15(17)39-23)41-27-25(21(35)19(33)16(8-28)40-27)42-26-22(36)18(32)14(31)9-38-26/h2-7,14,16,18-19,21-22,25-33,35-36H,8-9H2,1H3/t14-,16-,18+,19-,21+,22-,25-,26+,27+/m1/s1
• InChI Key: RLIQZPDFYSRCAD-QJQOJWJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4761	47.61%
Caco-2	-	0.9180	91.80%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.7057	70.57%
OATP1B1 inhibitior	+	0.8820	88.20%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7660	76.60%
P-glycoprotein inhibitior	-	0.5771	57.71%
P-glycoprotein substrate	-	0.5062	50.62%
CYP3A4 substrate	+	0.6878	68.78%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.9488	94.88%
CYP2C19 inhibition	-	0.9370	93.70%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	+	0.7456	74.56%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7584	75.84%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6674	66.74%
skin sensitisation	-	0.9265	92.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9315	93.15%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.8662	86.62%
Androgen receptor binding	+	0.6960	69.60%
Thyroid receptor binding	+	0.5684	56.84%
Glucocorticoid receptor binding	+	0.6192	61.92%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.7641	76.41%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.4193	41.93%

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	99.77%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.87%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.68%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.62%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.34%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.62%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	92.97%	91.49%
CHEMBL4208	P20618	Proteasome component C5	92.31%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.84%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.10%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.31%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.88%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.39%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	87.23%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.56%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.20%	95.83%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.89%	95.53%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.79%	92.62%

Plants that contains it

• Warburgia ugandensis

Cross-Links

• PubChem: 21576550
• LOTUS: LTS0153576
• wikiData: Q105240144