luteolin 7-O-[(beta-D-glucosyluronic acid)-(1->2)-(beta-D-glucosiduronic acid)] 4'-O-beta-D-glucosiduronic acid

Details

• Internal ID: cbe96ed1-1dd9-4aab-8d16-1fceb4f90378
• 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-[4-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]-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)OC6C(C(C(C(O6)C(=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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
• InChI: InChI=1S/C33H34O24/c34-9-3-7(1-2-12(9)53-31-22(43)16(37)18(39)24(54-31)28(45)46)13-6-11(36)15-10(35)4-8(5-14(15)52-13)51-33-27(21(42)20(41)26(56-33)30(49)50)57-32-23(44)17(38)19(40)25(55-32)29(47)48/h1-6,16-27,31-35,37-44H,(H,45,46)(H,47,48)(H,49,50)/t16-,17-,18-,19-,20-,21-,22+,23+,24-,25-,26-,27+,31+,32-,33+/m0/s1
• InChI Key: AEYXZGCDWDUIKX-OFFAAIFBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₄O₂₄
• Molecular Weight: 814.60 g/mol
• Exact Mass: 814.14400195 g/mol
• Topological Polar Surface Area (TPSA): 396.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -4.67
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 10

Synonyms

• luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide
• 2-[4-(beta-D-glucopyranosyloxyuronic acid)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl (beta-D-glucopyranosyluronic acid)-(1->2)-(beta-D-glucopyranosiduronic acid)
• 2-[4-(beta-D-glucopyranuronosyloxy)-3-hydroxyphenyl]-5-hydroxy-4-oxo-4H-chromen-7-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid
• C04900
• CHEBI:37645
• (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-6-carboxy-2-[2-[4-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• Q27104419

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.8810	88.10%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	-	0.5578	55.78%
OATP1B1 inhibitior	+	0.9529	95.29%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7466	74.66%
P-glycoprotein inhibitior	+	0.6842	68.42%
P-glycoprotein substrate	-	0.7304	73.04%
CYP3A4 substrate	+	0.6097	60.97%
CYP2C9 substrate	-	0.8160	81.60%
CYP2D6 substrate	-	0.8805	88.05%
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	+	0.8351	83.51%
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	-	0.8946	89.46%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.5364	53.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7505	75.05%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7782	77.82%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8549	85.49%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.7425	74.25%
Androgen receptor binding	+	0.6467	64.67%
Thyroid receptor binding	+	0.5264	52.64%
Glucocorticoid receptor binding	+	0.5631	56.31%
Aromatase binding	-	0.4854	48.54%
PPAR gamma	+	0.7072	70.72%
Honey bee toxicity	-	0.6712	67.12%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	99.06%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.58%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	97.49%	83.57%
CHEMBL3194	P02766	Transthyretin	97.26%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.07%	89.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	93.51%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.99%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.02%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.70%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.42%	86.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.36%	83.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.94%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.30%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.98%	99.17%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	86.02%	89.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.25%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.08%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.01%	81.11%
CHEMBL4531	P17931	Galectin-3	82.84%	96.90%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.37%	91.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.12%	97.36%
CHEMBL4530	P00488	Coagulation factor XIII	81.06%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	81.02%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.49%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.18%	99.23%

Plants that contains it

• Secale cereale

Cross-Links

• PubChem: 5280752
• LOTUS: LTS0271885
• wikiData: Q27104419