4',5,7-trihydroxy-3-methoxyflavone-7-O-alpha-L-arabinofuranosyl(1->6)-beta-D-glucopyranoside

Details

• Internal ID: 2cd5a680-e0d8-4b08-ad2c-c5345589b9ca
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-3-methoxychromen-4-one
• SMILES (Canonical): COC1=C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)COC4C(C(C(O4)CO)O)O)O)O)O)C5=CC=C(C=C5)O
• SMILES (Isomeric): COC1=C(OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O)C5=CC=C(C=C5)O
• InChI: InChI=1S/C27H30O15/c1-37-25-20(33)17-13(30)6-12(7-14(17)40-24(25)10-2-4-11(29)5-3-10)39-27-23(36)21(34)19(32)16(42-27)9-38-26-22(35)18(31)15(8-28)41-26/h2-7,15-16,18-19,21-23,26-32,34-36H,8-9H2,1H3/t15-,16+,18-,19+,21-,22+,23+,26+,27+/m0/s1
• InChI Key: CKDKWYQPVPNIAZ-SLJRIFGCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 4',5,7-trihydroxy-3-methoxyflavone-7-O-alpha-L-arabinofuranosyl(1->6)-beta-D-glucopyranoside
• CHEMBL1689263
• DTXSID401106194
• Q27136846
• 1266247-20-4
• 4H-1-Benzopyran-4-one, 7-[(6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-
• 5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside
• 7-[6-O-(alpha-L-Arabinofuranosyl)-beta-D-glucopyranosyloxy]-2-(4-hydroxyphenyl)-3-methoxy-5-hydroxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5974	59.74%
Caco-2	-	0.9234	92.34%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6848	68.48%
OATP2B1 inhibitior	-	0.5690	56.90%
OATP1B1 inhibitior	+	0.9035	90.35%
OATP1B3 inhibitior	+	0.9746	97.46%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7408	74.08%
P-glycoprotein inhibitior	-	0.6572	65.72%
P-glycoprotein substrate	-	0.5802	58.02%
CYP3A4 substrate	+	0.6244	62.44%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8638	86.38%
CYP2C9 inhibition	-	0.8003	80.03%
CYP2C19 inhibition	-	0.7529	75.29%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8921	89.21%
CYP2C8 inhibition	+	0.7870	78.70%
CYP inhibitory promiscuity	+	0.5065	50.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5707	57.07%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9182	91.82%
Skin irritation	-	0.8306	83.06%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7216	72.16%
Micronuclear	+	0.6833	68.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8970	89.70%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7667	76.67%
Acute Oral Toxicity (c)	III	0.7481	74.81%
Estrogen receptor binding	+	0.8083	80.83%
Androgen receptor binding	+	0.6216	62.16%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5744	57.44%
Aromatase binding	+	0.6359	63.59%
PPAR gamma	+	0.7125	71.25%
Honey bee toxicity	-	0.7784	77.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7431	74.31%

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	99.42%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.45%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.13%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.49%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.39%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.28%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.16%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.41%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	91.38%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.27%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.05%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.02%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.68%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.96%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.37%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.22%	95.89%
CHEMBL242	Q92731	Estrogen receptor beta	80.02%	98.35%

Plants that contains it

• Lepisorus contortus

Cross-Links

• PubChem: 51042404
• NPASS: NPC144131
• LOTUS: LTS0121503
• wikiData: Q27136846