luteolin-7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]

Details

• Internal ID: 353b6a86-4881-48f6-8dcf-d3eb096f8600
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-6-carboxy-2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxyoxan-3-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)OC5C(C(C(C(O5)C(=O)O)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)C(=O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H26O18/c28-9-2-1-7(3-10(9)29)13-6-12(31)15-11(30)4-8(5-14(15)42-13)41-27-23(19(35)18(34)22(44-27)25(39)40)45-26-20(36)16(32)17(33)21(43-26)24(37)38/h1-6,16-23,26-30,32-36H,(H,37,38)(H,39,40)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1
• InChI Key: PBBVWJQPAZYQDB-DBFWEQBMSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₈
• Molecular Weight: 638.50 g/mol
• Exact Mass: 638.11191398 g/mol
• Topological Polar Surface Area (TPSA): 300.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• 96400-45-2
• Luteolin 7-O-beta-D-diglucuronide
• luteolin-7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]
• luteolin-7-O-[beta-glucuronosyl-(1->2)-beta-glucuronide]
• (2S,3S,4S,5R,6R)-6-(((2S,3R,4S,5S,6S)-6-Carboxy-2-((2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
• CHEBI:60077
• HY-N7269
• C27H26O18
• AKOS040740834
• (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-6-carboxy-2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• MS-30898
• CS-0111085
• E87152
• Q27127061

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.9147	91.47%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	-	0.5501	55.01%
OATP1B1 inhibitior	+	0.9609	96.09%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5815	58.15%
P-glycoprotein inhibitior	-	0.5083	50.83%
P-glycoprotein substrate	-	0.8169	81.69%
CYP3A4 substrate	+	0.6089	60.89%
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	+	0.8376	83.76%
CYP inhibitory promiscuity	-	0.8051	80.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6914	69.14%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8972	89.72%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.5064	50.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.6678	66.78%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7282	72.82%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8946	89.46%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.6907	69.07%
Thyroid receptor binding	+	0.5264	52.64%
Glucocorticoid receptor binding	+	0.5542	55.42%
Aromatase binding	+	0.5299	52.99%
PPAR gamma	+	0.7362	73.62%
Honey bee toxicity	-	0.6451	64.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	99.80%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.64%	89.00%
CHEMBL3194	P02766	Transthyretin	96.24%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.60%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.76%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.48%	90.71%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.31%	83.57%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.86%	97.36%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.82%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.80%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.79%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.48%	83.00%
CHEMBL4531	P17931	Galectin-3	84.19%	96.90%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.82%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.39%	99.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.20%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.09%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.89%	81.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.59%	85.14%
CHEMBL4530	P00488	Coagulation factor XIII	80.44%	96.00%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.30%	89.23%

Plants that contains it

• Aconitum leucostomum
• Aiouea montana
• Aquilegia ecalcarata
• Artemisia szowitziana
• Blumea axillaris
• Ceanothus velutinus
• Chlorophytum borivilianum
• Dipterocarpus dyeri
• Elodea canadensis
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Lycopus europaeus
• Medicago truncatula
• Perilla frutescens
• Persea barbujana
• Secale cereale
• Verbena officinalis

Cross-Links

• PubChem: 5282153
• NPASS: NPC128988
• LOTUS: LTS0203367
• wikiData: Q27127061