5,4'-Dihydroxy-7-[6-O-(3-O-acetyl-alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]flavone

Details

• Internal ID: ae749538-e2fa-4431-93ed-2f8903bcc809
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2S,3S,4R,5R,6R)-3,5-dihydroxy-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]oxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)OC(=O)C)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=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)OC(=O)C)O
• InChI: InChI=1S/C29H32O15/c1-11-22(34)27(41-12(2)30)26(38)28(40-11)39-10-20-23(35)24(36)25(37)29(44-20)42-15-7-16(32)21-17(33)9-18(43-19(21)8-15)13-3-5-14(31)6-4-13/h3-9,11,20,22-29,31-32,34-38H,10H2,1-2H3/t11-,20+,22-,23+,24-,25+,26+,27+,28+,29+/m0/s1
• InChI Key: WXBYVUCALCQKLS-MRBYITRJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₂O₁₅
• Molecular Weight: 620.60 g/mol
• Exact Mass: 620.17412031 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.53
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6064	60.64%
Caco-2	-	0.8929	89.29%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7497	74.97%
OATP2B1 inhibitior	-	0.5660	56.60%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7502	75.02%
P-glycoprotein inhibitior	-	0.5852	58.52%
P-glycoprotein substrate	+	0.6033	60.33%
CYP3A4 substrate	+	0.6261	62.61%
CYP2C9 substrate	+	0.5319	53.19%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.9146	91.46%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.9514	95.14%
CYP2D6 inhibition	-	0.9627	96.27%
CYP1A2 inhibition	-	0.9472	94.72%
CYP2C8 inhibition	+	0.7068	70.68%
CYP inhibitory promiscuity	-	0.8213	82.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6655	66.55%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.8454	84.54%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6754	67.54%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.9440	94.40%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8859	88.59%
Acute Oral Toxicity (c)	III	0.6478	64.78%
Estrogen receptor binding	+	0.7685	76.85%
Androgen receptor binding	+	0.6267	62.67%
Thyroid receptor binding	-	0.5135	51.35%
Glucocorticoid receptor binding	+	0.6371	63.71%
Aromatase binding	+	0.5785	57.85%
PPAR gamma	+	0.7794	77.94%
Honey bee toxicity	-	0.7136	71.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.9238	92.38%

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	99.57%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.30%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	98.28%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.31%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.58%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.80%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.38%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.60%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.71%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.70%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.94%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.59%	86.92%
CHEMBL3194	P02766	Transthyretin	85.85%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.24%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.67%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.27%	81.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.17%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.50%	95.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.00%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.81%	94.80%
CHEMBL5255	O00206	Toll-like receptor 4	80.71%	92.50%

Plants that contains it

• Scoparia dulcis

Cross-Links

• PubChem: 11250565
• NPASS: NPC101636
• LOTUS: LTS0098615
• wikiData: Q105314506