5,6,7,4'-Tetrahydroxyflavonol 3-O-rutinoside

Details

• Internal ID: 77415969-13df-4555-9d28-54883d1bcb3e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-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=C(C3=O)C(=C(C(=C4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)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(OC4=C(C3=O)C(=C(C(=C4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-15(30)20(35)22(37)26(40-8)39-7-13-17(32)21(36)23(38)27(42-13)43-25-19(34)14-12(6-11(29)16(31)18(14)33)41-24(25)9-2-4-10(28)5-3-9/h2-6,8,13,15,17,20-23,26-33,35-38H,7H2,1H3/t8-,13+,15-,17+,20+,21-,22+,23+,26+,27-/m0/s1
• InChI Key: QYRJNVCANQPMCH-QGAVNTNWSA-N
• Popularity: 1 reference 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): 266.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 5,6,7,4'-Tetrahydroxyflavonol 3-O-rutinoside
• 5,6,7,4'-tetrahydroxyflavonol-3-O-rutinoside
• 6-Hydroxykaempferol 3-beta-rutinoside
• CHEBI:66215
• 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CHEMBL449793
• HY-N8191
• AKOS040760237
• 4',5,6,7-Tetrahydroxyflavonol 3-rutinoside
• CS-0140288
• E87176
• Q27134753
• 5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5564	55.64%
Caco-2	-	0.9289	92.89%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.5631	56.31%
OATP1B1 inhibitior	+	0.8762	87.62%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7041	70.41%
P-glycoprotein inhibitior	-	0.6327	63.27%
P-glycoprotein substrate	-	0.5268	52.68%
CYP3A4 substrate	+	0.6301	63.01%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.8336	83.36%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9027	90.27%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6627	66.27%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9325	93.25%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9471	94.71%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.6424	64.24%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.6508	65.08%
Aromatase binding	+	0.6475	64.75%
PPAR gamma	+	0.7419	74.19%
Honey bee toxicity	-	0.7788	77.88%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5350	53.50%
Fish aquatic toxicity	+	0.8993	89.93%

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	99.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.21%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.77%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.41%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.38%	95.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.38%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.18%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.92%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.73%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.42%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.85%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	89.58%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.49%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.79%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.23%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.81%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.78%	94.45%
CHEMBL3194	P02766	Transthyretin	82.38%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.95%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.93%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.84%	91.71%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 10371537
• NPASS: NPC65563
• LOTUS: LTS0214551
• wikiData: Q27134753