(2S)-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 330d17b1-e730-45ea-8f84-096a28b588c4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2S)-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2CC(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(O2)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CO)O)O)O)OC)O
• InChI: InChI=1S/C23H26O11/c1-30-11-6-16-19(13(26)8-15(32-16)10-3-4-14(31-2)12(25)5-10)17(7-11)33-23-22(29)21(28)20(27)18(9-24)34-23/h3-7,15,18,20-25,27-29H,8-9H2,1-2H3/t15-,18-,20+,21-,22+,23+/m0/s1
• InChI Key: NKYUUWHIEOUGKB-HCBKAOJGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₁
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.14751164 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• 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	-	0.8426	84.26%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6367	63.67%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7807	78.07%
CYP3A4 substrate	+	0.6114	61.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
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	-	0.5941	59.41%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4569	45.69%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5793	57.93%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8350	83.50%
Androgen receptor binding	-	0.6491	64.91%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.6076	60.76%
Aromatase binding	-	0.6215	62.15%
PPAR gamma	+	0.7560	75.60%
Honey bee toxicity	-	0.7804	78.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6849	68.49%
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	98.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.97%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.51%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.76%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.45%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.00%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.74%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.50%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.64%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.10%	94.45%
CHEMBL4208	P20618	Proteasome component C5	88.46%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.05%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.68%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.25%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	84.41%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.96%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.91%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.28%	92.62%

Plants that contains it

• Prunus persica

Cross-Links

• PubChem: 154497190
• LOTUS: LTS0234295
• wikiData: Q105181214