3,3',4'-Trihydroxyflavone 3-O-[a-L-rhamnopyranosyl-(1->2)[a-L-rhamnopyranosyl-(1->6)]-b-D-glucopyranoside]

Details

• Internal ID: 11292389-be89-4783-bd6c-2f86ed12f052
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]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)C5=CC(=C(C=C5)O)O)OC6C(C(C(C(O6)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC=CC=C4C3=O)C5=CC(=C(C=C5)O)O)OC6C(C(C(C(O6)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O18/c1-11-19(36)23(40)26(43)31(46-11)45-10-18-22(39)25(42)30(51-32-27(44)24(41)20(37)12(2)47-32)33(49-18)50-29-21(38)14-5-3-4-6-17(14)48-28(29)13-7-8-15(34)16(35)9-13/h3-9,11-12,18-20,22-27,30-37,39-44H,10H2,1-2H3
• InChI Key: ZOLZRMBQJLBHSS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₈
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.22146442 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.25
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• CHEBI:191990
• DTXSID901100496
• 2-(3,4-dihydroxyphenyl)-3-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
• 4H-1-Benzopyran-4-one, 3-[(O-6-deoxy-beta-L-mannopyranosyl-(1-->2)-O-[6-deoxy-beta-L-mannopyranosyl-(1-->6)]-beta-D-glucopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-
• 95880-20-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.9111	91.11%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	0.7133	71.33%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7979	79.79%
P-glycoprotein inhibitior	-	0.5478	54.78%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6742	67.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	-	0.8904	89.04%
CYP2C9 inhibition	-	0.9134	91.34%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.7553	75.53%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.8277	82.77%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3657	36.57%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9502	95.02%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.6578	65.78%
Thyroid receptor binding	+	0.5532	55.32%
Glucocorticoid receptor binding	+	0.5436	54.36%
Aromatase binding	+	0.5612	56.12%
PPAR gamma	+	0.7286	72.86%
Honey bee toxicity	-	0.7219	72.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9179	91.79%

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	99.91%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.50%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.99%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.49%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.23%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.67%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.48%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.52%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.43%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.64%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.89%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.61%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.54%	83.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.58%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.28%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.23%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.66%	93.65%

Plants that contains it

• Guioa crenulata

Cross-Links

• PubChem: 131752789
• LOTUS: LTS0115218
• wikiData: Q105380572