5,6,4'-Trihydroxy-7-[6-O-(2-O,3-O-diacetyl-alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]flavone

Details

• Internal ID: 70d30d26-6ff2-46f3-8c1a-1a730647acf7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2R,3R,4R,5S,6S)-3-acetyloxy-2-[[(2R,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-5-hydroxy-6-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)OC(=O)C)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=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)OC(=O)C)OC(=O)C)O
• InChI: InChI=1S/C31H34O17/c1-11-22(36)28(44-12(2)32)29(45-13(3)33)31(43-11)42-10-20-24(38)26(40)27(41)30(48-20)47-19-9-18-21(25(39)23(19)37)16(35)8-17(46-18)14-4-6-15(34)7-5-14/h4-9,11,20,22,24,26-31,34,36-41H,10H2,1-3H3/t11-,20+,22-,24+,26-,27+,28+,29+,30+,31+/m0/s1
• InChI Key: SBKDMCQRDPOEID-QWRLEPBMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₄O₁₇
• Molecular Weight: 678.60 g/mol
• Exact Mass: 678.17959961 g/mol
• Topological Polar Surface Area (TPSA): 257.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 5,6,4'-Trihydroxy-7-[6-O-(2-O,3-O-diacetyl-alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]flavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5722	57.22%
Caco-2	-	0.8867	88.67%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7010	70.10%
OATP2B1 inhibitior	-	0.5617	56.17%
OATP1B1 inhibitior	+	0.7314	73.14%
OATP1B3 inhibitior	+	0.9026	90.26%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6869	68.69%
P-glycoprotein inhibitior	-	0.4313	43.13%
P-glycoprotein substrate	+	0.5805	58.05%
CYP3A4 substrate	+	0.6531	65.31%
CYP2C9 substrate	+	0.5334	53.34%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.9237	92.37%
CYP2C19 inhibition	-	0.9484	94.84%
CYP2D6 inhibition	-	0.9669	96.69%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	+	0.7723	77.23%
CYP inhibitory promiscuity	-	0.8269	82.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9101	91.01%
Skin irritation	-	0.8540	85.40%
Skin corrosion	-	0.9598	95.98%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4063	40.63%
Micronuclear	+	0.6992	69.92%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9393	93.93%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9269	92.69%
Acute Oral Toxicity (c)	III	0.6145	61.45%
Estrogen receptor binding	+	0.8038	80.38%
Androgen receptor binding	+	0.6776	67.76%
Thyroid receptor binding	+	0.5169	51.69%
Glucocorticoid receptor binding	+	0.6771	67.71%
Aromatase binding	+	0.6030	60.30%
PPAR gamma	+	0.7668	76.68%
Honey bee toxicity	-	0.7040	70.40%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.9438	94.38%

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	99.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.99%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.82%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.55%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.63%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.01%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.03%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.92%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.78%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.70%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.27%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.25%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	90.02%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.01%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.32%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.95%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.82%	96.21%
CHEMBL3194	P02766	Transthyretin	81.57%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.86%	99.15%
CHEMBL5255	O00206	Toll-like receptor 4	80.60%	92.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.38%	81.11%

Plants that contains it

• Scoparia dulcis

Cross-Links

• PubChem: 11445323
• NPASS: NPC141356