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Quercetin 3-O-glucuronide

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)OC1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21?/m0/s1
InChIKey	DUBCCGAQYVUYEU-MBIBTLSJSA-N
Formula	C₂₁H₁₈O₁₃
HBA	12
HBD	8
MW	478.36
Rotatable Bonds	4
TPSA	227.58
LogP	-0.45
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	478.07
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Epilobium hirsutum	Onagraceae	Plantae	210355
2	Tamarix articulata	Tamaricaceae	Plantae	189786

Showing of synonyms

Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]
Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]

Pubchem: 13258914

Gnps: CCMSLIB00004706239

CPRiL: 87483

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.36 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.36 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 478.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.82
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.79
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 74.75
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.56
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.2
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.48
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -150.95
Rat (Acute): 2.25
Rat (Chronic Oral): 4.26
Fathead Minnow: 3.81
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 676.27
Hydration Free Energy: -4.32
Log(D) at pH=7.4: -1.59
Log(P): 0.7
Log S: -3.78
Log(Vapor Pressure): -12.59
Melting Point: 215.9
pKa Acid: 3.61
pKa Basic: 8.04

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9006
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9006
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8902
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8902
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8731
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8731
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8719
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8719
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8703
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8703
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8500
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8500
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8459
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8459
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8343
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8343
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8301
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8301
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8254
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8254
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8060
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8060
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7986
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7986
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7945
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7945
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7866
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7866
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7851
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7851
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7738
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7738
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7621
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7621
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7579
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7579
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7392
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7392
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7292
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7292
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7196
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7196
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7189
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7189
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7144
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7144
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7117
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7117
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7060
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7060

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