2-(3,4-Dimethoxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 6254d3b7-1c3f-4c59-a5db-0b5d439f089b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)OC)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)OC)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-11-22(32)24(34)26(36)28(41-11)40-10-20-23(33)25(35)27(37)29(44-20)42-13-7-14(30)21-15(31)9-17(43-19(21)8-13)12-4-5-16(38-2)18(6-12)39-3/h4-8,11,17,20,22-30,32-37H,9-10H2,1-3H3
• InChI Key: GUMSHIGGVOJLBP-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.85
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• Methylhesperidin
• 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• 11013-97-1
• CCRIS 4278
• C29-H36-O15
• DTXSID00860085
• BCP13743
• FT-0630386
• 2-(3,4-Dimethoxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8731	87.31%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.7230	72.30%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7204	72.04%
P-glycoprotein inhibitior	-	0.7645	76.45%
P-glycoprotein substrate	+	0.5089	50.89%
CYP3A4 substrate	+	0.6378	63.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9351	93.51%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	+	0.5624	56.24%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9243	92.43%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7687	76.87%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7426	74.26%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.8222	82.22%
Androgen receptor binding	-	0.8513	85.13%
Thyroid receptor binding	+	0.5730	57.30%
Glucocorticoid receptor binding	+	0.6309	63.09%
Aromatase binding	-	0.4887	48.87%
PPAR gamma	+	0.6976	69.76%
Honey bee toxicity	-	0.7279	72.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8533	85.33%

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	99.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.48%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.72%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.81%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.71%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.65%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.58%	94.00%
CHEMBL4208	P20618	Proteasome component C5	92.67%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.62%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.09%	97.36%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.08%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.65%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.53%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.15%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.78%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	84.25%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.21%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.74%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.37%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.24%	99.15%
CHEMBL2535	P11166	Glucose transporter	82.05%	98.75%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.05%	92.38%

Plants that contains it

• Plantago asiatica
• Plantago depressa

Cross-Links

• PubChem: 4613731
• NPASS: NPC184881