Luteolin 5-glucoside

Details

• Internal ID: 046550b2-ec83-4b73-b849-026f775a45cd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,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(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-15-5-9(23)4-14-17(15)12(26)6-13(30-14)8-1-2-10(24)11(25)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
• InChI Key: KBGKQZVCLWKUDQ-QNDFHXLGSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• Luteolin 5-glucoside
• Luteolin-5-O-glucoside
• Galuteolin
• Luteollin 5-glucoside
• Luteolin 5-O-glucoside
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-(beta-D-glucopyranosyloxy)-7-hydroxy-
• CNI9E8ORF6
• Luteolin-5-O-beta-D-glucoside
• luteolin-5-o-beta-d-glucopyranoside
• 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-(.beta.-D-glucopyranosyloxy)-7-hydroxy-
• Luteollin5-glucoside
• UNII-CNI9E8ORF6
• Luteolin-5-O-glucopyranoside
• SCHEMBL242602
• DTXSID30942500
• LUTEOLIN 5-GLUCOSIDE [MI]
• HY-N2008
• AKOS016010674
• PD164892
• CS-0018328
• LUTEOLIN 5-O-.BETA.-D-GLUCOPYRANOSIDE
• A879702
• Q-100249
• 2-(3,4-Dihydroxyphenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-5-yl hexopyranoside
• 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9307	93.07%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5933	59.33%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6887	68.87%
P-glycoprotein inhibitior	-	0.7450	74.50%
P-glycoprotein substrate	-	0.8155	81.55%
CYP3A4 substrate	+	0.5733	57.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.7449	74.49%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8464	84.64%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5090	50.90%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8321	83.21%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7019	70.19%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7242	72.42%
Androgen receptor binding	+	0.7257	72.57%
Thyroid receptor binding	+	0.5632	56.32%
Glucocorticoid receptor binding	+	0.6878	68.78%
Aromatase binding	+	0.5414	54.14%
PPAR gamma	+	0.7568	75.68%
Honey bee toxicity	-	0.6598	65.98%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6599	65.99%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.49%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.84%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.27%	98.95%
CHEMBL3194	P02766	Transthyretin	94.07%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.75%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.64%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.33%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.79%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.72%	95.78%
CHEMBL220	P22303	Acetylcholinesterase	89.27%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.66%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	86.94%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.07%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.18%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.94%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.37%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.45%	85.14%

Plants that contains it

• Alangium ridleyi
• Artemisia rupestris
• Carlina acaulis
• Chrysanthemum morifolium
• Daphne genkwa
• Elsholtzia rugulosa
• Equisetum arvense
• Galega officinalis
• Gentiana arisanensis
• Halleria lucida
• Hedysarum denticulatum
• Helichrysum nitens
• Hydrocotyle ranunculoides
• Hypericum perforatum
• Lawsonia inermis
• Leycesteria formosa
• Ligularia songarica
• Lippia origanoides
• Lotus pedunculatus
• Marrubium cylleneum
• Mayaca fluviatilis
• Morinda morindoides
• Nelumbo nucifera
• Ocimum tenuiflorum
• Osmanthus heterophyllus
• Salix cheilophila
• Scorzonera pseudodivaricata
• Senecio nemorensis
• Spiraea hypericifolia
• Tinospora crispa
• Torilis arvensis
• Verbascum lychnitis

Cross-Links

• PubChem: 5317471
• NPASS: NPC228834
• LOTUS: LTS0155853
• wikiData: Q72487810