Lutonarin

Details

• Internal ID: e44b0acc-9f16-45b3-9199-bb1d3a56db8b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c28-6-15-19(33)22(36)24(38)26(41-15)18-14(42-27-25(39)23(37)20(34)16(7-29)43-27)5-13-17(21(18)35)11(32)4-12(40-13)8-1-2-9(30)10(31)3-8/h1-5,15-16,19-20,22-31,33-39H,6-7H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
• InChI Key: OQKYVRDRDIXQMK-KETMJRJWSA-N
• Popularity: 3 references 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): 277.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.73
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 6

Synonyms

• 35450-86-3
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-7-(beta-D-glucopyranosyloxy)-5-hydroxy-
• CHEMBL470327
• DTXSID601318676
• HY-N9585
• AKOS040762744
• CS-0201482
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9277	92.77%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5564	55.64%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5565	55.65%
P-glycoprotein inhibitior	-	0.6056	60.56%
P-glycoprotein substrate	-	0.7187	71.87%
CYP3A4 substrate	+	0.6008	60.08%
CYP2C9 substrate	-	0.6621	66.21%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.7518	75.18%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8946	89.46%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6235	62.35%
Human Ether-a-go-go-Related Gene inhibition	+	0.7243	72.43%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8037	80.37%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9025	90.25%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7470	74.70%
Androgen receptor binding	+	0.6850	68.50%
Thyroid receptor binding	+	0.5147	51.47%
Glucocorticoid receptor binding	-	0.5881	58.81%
Aromatase binding	+	0.5924	59.24%
PPAR gamma	+	0.7657	76.57%
Honey bee toxicity	-	0.6718	67.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.65%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.93%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.60%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.58%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.46%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.37%	96.21%
CHEMBL220	P22303	Acetylcholinesterase	91.89%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.40%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.46%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.92%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.75%	95.56%
CHEMBL3194	P02766	Transthyretin	85.02%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.69%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.50%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.00%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.49%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.36%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.67%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.12%	95.89%

Plants that contains it

• Bryonia alba
• Hordeum vulgare
• Plagiomnium cuspidatum
• Triticum aestivum
• Vellozia coronata

Cross-Links

• PubChem: 44559810
• LOTUS: LTS0042153
• wikiData: Q104391954