Luteolin-7-o-glucuronide

Details

• Internal ID: 5e9ba951-89cc-4cd4-811c-ccba7857af3c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: 6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)
• InChI Key: VSUOKLTVXQRUSG-UHFFFAOYSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₁₂
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.07982601 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• Luteolin-7-beta-D-glucuronide
• 6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SCHEMBL24449203
• BCP29714
• 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-1-benzopyran-7-yl-|A-D-glucopyranosiduronic acid
• 3 inverted exclamation marka,4 inverted exclamation marka,5,7-Tetrahydroxy-7-|A-D-glucopyranuronoside flavone
• Luteolin-7-glucuronide;Luteolin 7-O-beta-D-glucuronopyranoside; Luteolin 7-O-beta-glucuronide;Luteolin 7-O-beta-glucuronopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.9351	93.51%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	-	0.5033	50.33%
OATP1B1 inhibitior	+	0.9687	96.87%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4752	47.52%
P-glycoprotein inhibitior	-	0.7226	72.26%
P-glycoprotein substrate	-	0.8998	89.98%
CYP3A4 substrate	+	0.5605	56.05%
CYP2C9 substrate	-	0.8166	81.66%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.7354	73.54%
CYP2C9 inhibition	-	0.7205	72.05%
CYP2C19 inhibition	-	0.8328	83.28%
CYP2D6 inhibition	-	0.9625	96.25%
CYP1A2 inhibition	-	0.7704	77.04%
CYP2C8 inhibition	+	0.8601	86.01%
CYP inhibitory promiscuity	-	0.8051	80.51%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6914	69.14%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8527	85.27%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.5264	52.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5156	51.56%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7407	74.07%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8566	85.66%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.7394	73.94%
Androgen receptor binding	+	0.7301	73.01%
Thyroid receptor binding	-	0.4920	49.20%
Glucocorticoid receptor binding	+	0.6828	68.28%
Aromatase binding	-	0.5569	55.69%
PPAR gamma	+	0.7102	71.02%
Honey bee toxicity	-	0.7047	70.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9599	95.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.55%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.36%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.18%	89.00%
CHEMBL3194	P02766	Transthyretin	96.16%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.12%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.03%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.24%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.05%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.09%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	85.47%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.18%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.51%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.83%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.69%	83.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.66%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.84%	85.14%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.75%	95.64%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.62%	97.36%

Plants that contains it

• Acanthus ebracteatus
• Achillea collina
• Agrimonia eupatoria
• Chrysanthemum indicum
• Dumortiera hirsuta
• Gymnanthemum amygdalinum
• Inulanthera nuda
• Lactuca indica
• Lycopus asper
• Marrubium vulgare
• Medicago sativa
• Medicago truncatula
• Meehania fargesii
• Meehania urticifolia
• Monarda punctata
• Ocimum gratissimum
• Origanum vulgare
• Pedicularis longiflora
• Penstemon serrulatus
• Perilla frutescens
• Phagnalon rupestre
• Potentilla anserina
• Salvia fruticosa
• Salvia officinalis
• Scutellaria galericulata
• Scutellaria iskanderi
• Scutellaria phyllostachya
• Sonchus arvensis
• Sonchus erzincanicus
• Tanacetum parthenium
• Trifolium pannonicum
• Tripora divaricata
• Youngia japonica

Cross-Links

• PubChem: 13607752
• LOTUS: LTS0175049
• wikiData: Q104389857