3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: bd67a733-5baa-4ae3-b802-6fd73bf0bd6b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(CO4)O)O)O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(CO4)O)O)O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C27H30O15/c1-37-12-6-13(30)17-15(7-12)39-23(10-2-4-11(29)5-3-10)24(20(17)34)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
• InChI Key: OBDMFJQEVDKJHR-UHFFFAOYSA-N
• Popularity: 0 references 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	-	0.9223	92.23%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5114	51.14%
OATP2B1 inhibitior	-	0.7080	70.80%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.9679	96.79%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7420	74.20%
P-glycoprotein inhibitior	-	0.5588	55.88%
P-glycoprotein substrate	-	0.5164	51.64%
CYP3A4 substrate	+	0.6742	67.42%
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	+	0.7228	72.28%
CYP inhibitory promiscuity	-	0.8596	85.96%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6677	66.77%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.8242	82.42%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3803	38.03%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6351	63.51%
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	-	0.9330	93.30%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.8383	83.83%
Androgen receptor binding	+	0.7076	70.76%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.5786	57.86%
Aromatase binding	+	0.6135	61.35%
PPAR gamma	+	0.7404	74.04%
Honey bee toxicity	-	0.7552	75.52%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	99.67%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.89%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.90%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.51%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.31%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.39%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.28%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.11%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.77%	95.64%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.35%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	88.24%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	88.10%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.07%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.73%	99.17%
CHEMBL4208	P20618	Proteasome component C5	86.78%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.29%	95.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.24%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.08%	95.89%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.79%	93.10%

Plants that contains it

• Alstonia balansae
• Phytolacca thyrsiflora

Cross-Links

• PubChem: 14132382
• LOTUS: LTS0008180
• wikiData: Q105363746