2-(3-Methoxy-4-hydroxyphenyl)-3-[2-O,6-O-bis(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]-5-hydroxy-7-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one

Details

• Internal ID: 214cd7a3-3bd4-47b5-a195-1ca81488e349
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=C(C=C6)O)OC)OC7C(C(C(C(O7)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=C(C=C6)O)OC)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C40H52O25/c1-11-22(44)27(49)31(53)37(58-11)57-10-20-25(47)30(52)36(65-38-32(54)28(50)23(45)12(2)59-38)40(63-20)64-35-26(48)21-16(43)7-14(60-39-33(55)29(51)24(46)19(9-41)62-39)8-18(21)61-34(35)13-4-5-15(42)17(6-13)56-3/h4-8,11-12,19-20,22-25,27-33,36-47,49-55H,9-10H2,1-3H3/t11-,12-,19+,20+,22-,23-,24+,25+,27+,28+,29-,30-,31+,32+,33+,36+,37+,38-,39+,40-/m0/s1
• InChI Key: BPSWMCGRCGOHIN-LAEAVMHESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₂O₂₅
• Molecular Weight: 932.80 g/mol
• Exact Mass: 932.27976714 g/mol
• Topological Polar Surface Area (TPSA): 393.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -5.06
• H-Bond Acceptor: 25
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5613	56.13%
Caco-2	-	0.9006	90.06%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5797	57.97%
OATP2B1 inhibitior	-	0.7224	72.24%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8283	82.83%
P-glycoprotein inhibitior	+	0.6356	63.56%
P-glycoprotein substrate	+	0.6608	66.08%
CYP3A4 substrate	+	0.6664	66.64%
CYP2C9 substrate	-	0.8740	87.40%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.9607	96.07%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	-	0.9294	92.94%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.9319	93.19%
CYP2C8 inhibition	+	0.8142	81.42%
CYP inhibitory promiscuity	-	0.7425	74.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6863	68.63%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.8525	85.25%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.6692	66.92%
Human Ether-a-go-go-Related Gene inhibition	+	0.7598	75.98%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9360	93.60%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8989	89.89%
Acute Oral Toxicity (c)	III	0.7015	70.15%
Estrogen receptor binding	+	0.7993	79.93%
Androgen receptor binding	+	0.5603	56.03%
Thyroid receptor binding	+	0.5420	54.20%
Glucocorticoid receptor binding	+	0.5618	56.18%
Aromatase binding	-	0.4870	48.70%
PPAR gamma	+	0.7400	74.00%
Honey bee toxicity	-	0.6882	68.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.7238	72.38%

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	99.48%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.80%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.22%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.36%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.31%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.03%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.32%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.83%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.27%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.91%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.52%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.28%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	89.59%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.90%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.90%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.91%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.62%	97.09%
CHEMBL3194	P02766	Transthyretin	82.95%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.05%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.75%	96.21%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 101857081
• NPASS: NPC123463
• LOTUS: LTS0077770
• wikiData: Q104943867