2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one

Details

• Internal ID: 97cf9515-423b-4c59-9598-c58397f46907
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(CO4)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c1-8-17(31)20(34)22(36)26(38-8)39-10-5-13(29)16-15(6-10)40-23(9-2-3-11(27)12(28)4-9)24(19(16)33)41-25-21(35)18(32)14(30)7-37-25/h2-6,8,14,17-18,20-22,25-32,34-36H,7H2,1H3/t8-,14+,17-,18-,20+,21+,22+,25-,26-/m0/s1
• InChI Key: LKCWNKWQDHJLCT-OAQZHQCOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7160	71.60%
Caco-2	-	0.9091	90.91%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6720	67.20%
OATP2B1 inhibitior	-	0.5560	55.60%
OATP1B1 inhibitior	+	0.9482	94.82%
OATP1B3 inhibitior	+	0.8917	89.17%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7835	78.35%
P-glycoprotein inhibitior	-	0.5490	54.90%
P-glycoprotein substrate	-	0.5309	53.09%
CYP3A4 substrate	+	0.6598	65.98%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9278	92.78%
CYP2C9 inhibition	-	0.9538	95.38%
CYP2C19 inhibition	-	0.9355	93.55%
CYP2D6 inhibition	-	0.9268	92.68%
CYP1A2 inhibition	-	0.8650	86.50%
CYP2C8 inhibition	+	0.7991	79.91%
CYP inhibitory promiscuity	-	0.8976	89.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6476	64.76%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8896	88.96%
Skin irritation	-	0.7836	78.36%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.6099	60.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.7490	74.90%
Micronuclear	+	0.7433	74.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9187	91.87%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9520	95.20%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.7508	75.08%
Androgen receptor binding	+	0.6476	64.76%
Thyroid receptor binding	-	0.5305	53.05%
Glucocorticoid receptor binding	+	0.6232	62.32%
Aromatase binding	-	0.5134	51.34%
PPAR gamma	+	0.7046	70.46%
Honey bee toxicity	-	0.7182	71.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.8557	85.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.79%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.63%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.75%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.44%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.15%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.91%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.96%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.92%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.52%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.60%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.02%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.56%	96.09%
CHEMBL4208	P20618	Proteasome component C5	88.35%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.52%	95.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.11%	95.64%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.39%	95.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.64%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.41%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.21%	95.89%

Plants that contains it

• Hibiscus syriacus

Cross-Links

• PubChem: 162972958
• LOTUS: LTS0119712
• wikiData: Q105152994