5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one

Details

• Internal ID: c893e11f-2b6b-4ad3-ace0-a5f1ae3d3c0b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)C4C(C(C(CO4)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O
• InChI: InChI=1S/C22H22O11/c1-30-13-3-8(4-14(31-2)18(13)27)21-16(22-20(29)17(26)11(25)7-32-22)19(28)15-10(24)5-9(23)6-12(15)33-21/h3-6,11,17,20,22-27,29H,7H2,1-2H3/t11-,17-,20+,22-/m0/s1
• InChI Key: RECSNXAWHKPBJA-FPOPXEHXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8025	80.25%
Caco-2	-	0.8011	80.11%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6095	60.95%
OATP2B1 inhibitior	+	0.5780	57.80%
OATP1B1 inhibitior	+	0.8590	85.90%
OATP1B3 inhibitior	+	0.9694	96.94%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6639	66.39%
P-glycoprotein inhibitior	-	0.4421	44.21%
P-glycoprotein substrate	+	0.5744	57.44%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.8241	82.41%
CYP3A4 inhibition	-	0.6430	64.30%
CYP2C9 inhibition	-	0.9294	92.94%
CYP2C19 inhibition	-	0.8663	86.63%
CYP2D6 inhibition	-	0.8367	83.67%
CYP1A2 inhibition	-	0.7517	75.17%
CYP2C8 inhibition	+	0.8102	81.02%
CYP inhibitory promiscuity	-	0.8430	84.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6806	68.06%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8316	83.16%
Skin irritation	-	0.7905	79.05%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6148	61.48%
Micronuclear	+	0.7359	73.59%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.9144	91.44%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8976	89.76%
Acute Oral Toxicity (c)	III	0.6897	68.97%
Estrogen receptor binding	+	0.8512	85.12%
Androgen receptor binding	+	0.7216	72.16%
Thyroid receptor binding	+	0.5380	53.80%
Glucocorticoid receptor binding	+	0.8360	83.60%
Aromatase binding	-	0.5357	53.57%
PPAR gamma	+	0.7422	74.22%
Honey bee toxicity	-	0.7912	79.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.6758	67.58%

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	99.35%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.89%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.05%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.25%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.24%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.42%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.84%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.71%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.40%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	83.33%	94.73%
CHEMBL3194	P02766	Transthyretin	83.17%	90.71%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.28%	96.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.17%	95.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.98%	94.45%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.68%	98.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.91%	94.03%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.57%	83.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.35%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.24%	95.53%

Plants that contains it

• Elegia microcarpa

Cross-Links

• PubChem: 162994953
• LOTUS: LTS0031082
• wikiData: Q105234632