3-[(6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy]-4',5,7-trihydroxy-3'-methoxyflavone

Details

• Internal ID: 93d191ca-ac05-41ce-a2bd-f25541d2fcbe
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-38-14-4-9(2-3-11(14)29)24-25(20(34)17-12(30)5-10(28)6-15(17)41-24)43-27-23(37)21(35)19(33)16(42-27)8-40-26-22(36)18(32)13(31)7-39-26/h2-6,13,16,18-19,21-23,26-33,35-37H,7-8H2,1H3/t13-,16-,18+,19-,21+,22-,23-,26+,27+/m1/s1
• InChI Key: HIRWMGZVIYIRJM-HXMOASODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.77
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• 142905-19-9
• 3-[(6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy]-4',5,7-trihydroxy-3'-methoxyflavone
• 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(6-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5869	58.69%
Caco-2	-	0.9266	92.66%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6520	65.20%
OATP2B1 inhibitior	-	0.5735	57.35%
OATP1B1 inhibitior	+	0.9046	90.46%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6005	60.05%
P-glycoprotein inhibitior	-	0.5695	56.95%
P-glycoprotein substrate	+	0.5539	55.39%
CYP3A4 substrate	+	0.6681	66.81%
CYP2C9 substrate	-	0.8664	86.64%
CYP2D6 substrate	-	0.8478	84.78%
CYP3A4 inhibition	-	0.9412	94.12%
CYP2C9 inhibition	-	0.9439	94.39%
CYP2C19 inhibition	-	0.8989	89.89%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	-	0.9037	90.37%
CYP2C8 inhibition	+	0.8439	84.39%
CYP inhibitory promiscuity	-	0.8756	87.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6679	66.79%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9013	90.13%
Skin irritation	-	0.8291	82.91%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6074	60.74%
Hepatotoxicity	-	0.6299	62.99%
skin sensitisation	-	0.9195	91.95%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9426	94.26%
Acute Oral Toxicity (c)	III	0.6736	67.36%
Estrogen receptor binding	+	0.8580	85.80%
Androgen receptor binding	+	0.6368	63.68%
Thyroid receptor binding	+	0.5246	52.46%
Glucocorticoid receptor binding	+	0.6405	64.05%
Aromatase binding	+	0.6035	60.35%
PPAR gamma	+	0.7572	75.72%
Honey bee toxicity	-	0.7747	77.47%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	+	0.8179	81.79%

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	99.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.86%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.63%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.52%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.41%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.79%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.89%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.53%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.46%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.37%	95.64%
CHEMBL220	P22303	Acetylcholinesterase	88.98%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.71%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.70%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.06%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	86.29%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.27%	97.09%
CHEMBL4208	P20618	Proteasome component C5	86.08%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.43%	95.53%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.47%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.41%	95.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.56%	92.62%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.68%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.53%	96.00%

Plants that contains it

• Amaranthus hypochondriacus
• Berberis repens
• Cistus ladanifer
• Croton laccifer
• Euphorbia myrsinites
• Helicteres angustifolia
• Hippeastrum papilio
• Limnocharis flava
• Lycopodium thyoides
• Millettia ferruginea
• Sedum litoreum
• Senecio viscosus
• Teucrium asiaticum
• Thermopsis dolichocarpa
• Vicia amurensis
• Wyethia mollis
• Zanthoxylum americanum

Cross-Links

• PubChem: 102148697
• NPASS: NPC141550
• LOTUS: LTS0133832
• wikiData: Q105028980