HYPOLAETIN 8-O-beta-D-GLUCURONIDE

Details

• Internal ID: f42a1b42-7233-4cbd-b7fc-a3b61fa3bf56
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-8-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C21H18O13/c22-7-2-1-6(3-8(7)23)12-5-10(25)13-9(24)4-11(26)17(18(13)32-12)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-24,26-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
• InChI Key: BVMDSEFJGKQBKJ-ZUGPOPFOSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₁₃
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.07474062 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.45
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• SNF5N3QC4V
• Hypolaetin 8-o-glucuronide
• 8-Hydroxyluteolin 8-glucuronide
• Hypolaetin 8-O-beta-D-glucuronide
• (2S,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• 56324-52-8
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranosiduronic acid
• beta-D-Glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-8-yl
• UNII-SNF5N3QC4V
• CHEMBL512433
• HYPOLAETIN 8-O-.BETA.-D-GLUCURONIDE
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-8-YL
• 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-8-YL .BETA.-D-GLUCOPYRANOSIDURONIC ACID
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-8-[(beta-D-glucopyranuronosyl)oxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7086	70.86%
Caco-2	-	0.9212	92.12%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6482	64.82%
OATP2B1 inhibitior	+	0.6017	60.17%
OATP1B1 inhibitior	+	0.9391	93.91%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4741	47.41%
P-glycoprotein inhibitior	-	0.6520	65.20%
P-glycoprotein substrate	-	0.8789	87.89%
CYP3A4 substrate	+	0.5699	56.99%
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	+	0.7978	79.78%
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	-	0.8379	83.79%
Skin irritation	-	0.6185	61.85%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.6064	60.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5693	56.93%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6250	62.50%
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	-	0.8867	88.67%
Acute Oral Toxicity (c)	II	0.4816	48.16%
Estrogen receptor binding	+	0.6750	67.50%
Androgen receptor binding	+	0.7604	76.04%
Thyroid receptor binding	-	0.5434	54.34%
Glucocorticoid receptor binding	+	0.6450	64.50%
Aromatase binding	-	0.6245	62.45%
PPAR gamma	+	0.6075	60.75%
Honey bee toxicity	-	0.7283	72.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
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	99.47%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.10%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.67%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.04%	99.15%
CHEMBL3194	P02766	Transthyretin	93.98%	90.71%
CHEMBL2581	P07339	Cathepsin D	91.93%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.02%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.85%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.05%	94.00%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.83%	89.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.56%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.48%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.87%	83.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.83%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.93%	99.23%

Plants that contains it

• Cosmos sulphureus
• Lavandula antineae
• Lavandula coronopifolia
• Malva sylvestris
• Ophiopogon japonicus
• Roemeria hispida
• Tanacetum argenteum
• Thamnosma rhodesica
• Theobroma grandiflorum

Cross-Links

• PubChem: 14887605
• NPASS: NPC135277
• LOTUS: LTS0104676
• wikiData: Q104946640