5-hydroxy-2-[3-hydroxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-6,7-dimethoxychromen-4-one

Details

• Internal ID: ed423ce1-f7f8-4fa3-9e4a-304c3f2a3da2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 5-hydroxy-2-[3-hydroxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-6,7-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O)OC
• InChI: InChI=1S/C23H24O12/c1-31-15-7-14-17(19(28)22(15)32-2)11(26)6-13(33-14)9-3-4-12(10(25)5-9)34-23-21(30)20(29)18(27)16(8-24)35-23/h3-7,16,18,20-21,23-25,27-30H,8H2,1-2H3/t16-,18-,20+,21-,23-/m0/s1
• InChI Key: GLTCTFBPNQJRQT-UTMPCQRGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₂
• Molecular Weight: 492.40 g/mol
• Exact Mass: 492.12677620 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8587	85.87%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5583	55.83%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5586	55.86%
P-glycoprotein inhibitior	-	0.4884	48.84%
P-glycoprotein substrate	-	0.5553	55.53%
CYP3A4 substrate	+	0.5967	59.67%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.7623	76.23%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5287	52.87%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9378	93.78%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8030	80.30%
Androgen receptor binding	+	0.6333	63.33%
Thyroid receptor binding	+	0.5960	59.60%
Glucocorticoid receptor binding	+	0.6592	65.92%
Aromatase binding	+	0.5236	52.36%
PPAR gamma	+	0.7750	77.50%
Honey bee toxicity	-	0.7469	74.69%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7449	74.49%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.00%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.57%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.75%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.91%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.52%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.13%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.94%	96.21%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.66%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.47%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.21%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.01%	99.15%
CHEMBL3194	P02766	Transthyretin	86.06%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.66%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	84.92%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.36%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.20%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.16%	95.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.04%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.87%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.30%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.04%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.11%	95.83%

Plants that contains it

• Artemisia annua
• Cirsium chinense
• Salvia officinalis
• Sium suave

Cross-Links

• PubChem: 11972311
• NPASS: NPC281385
• LOTUS: LTS0236844
• wikiData: Q105011272