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Quercetin-3-O-beta-D-glucouronide butyl ester

Family: Plantae - Vitaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	c1(c(c(=O)c2c(O)cc(O)cc2o1)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)C(=O)OCCCC)c1cc(O)c(O)cc1
InChI	InChI=1S/C25H26O13/c1-2-3-6-35-24(34)23-19(32)18(31)20(33)25(38-23)37-22-17(30)16-14(29)8-11(26)9-15(16)36-21(22)10-4-5-12(27)13(28)7-10/h4-5,7-9,18-20,23,25-29,31-33H,2-3,6H2,1H3/t18-,19-,20+,23-,25+/m0/s1
InChIKey	INCAPNMMVMDQPT-PNRYVWDLSA-N
Formula	C₂₅H₂₆O₁₃
HBA	13
HBD	7
MW	534.47
Rotatable Bonds	7
TPSA	216.58
LogP	0.81
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	534.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Vitis vinifera	Vitaceae	Plantae	29760

Showing of synonyms

Elraey M, Elgamal A. (2022). Quercetin-3-O-β-D-glucouronide butyl ester from Vitis vinifera leaves of potent antihelicobacter pylori activity and impact of its combination with clarithromycin. Egypt. J. Chem,2022,65(10),609-615. [View]

Pubchem: 102155866

Cas: 166196-16-3

Zinc: ZINC000059733032

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 534.47 g/mol

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

Level: 1

Mol. Weight: 534.47 g/mol

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

Level: 1

Mol. Weight: 534.47 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 534.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 534.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 534.47 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.66
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.33
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.9
Plasma Protein Binding: 78.73
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: 14.35
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.17
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.4
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: -1128.08
Rat (Acute): 2.35
Rat (Chronic Oral): 4.0
Fathead Minnow: 5.23
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 630.57
Hydration Free Energy: -3.15
Log(D) at pH=7.4: 1.42
Log(P): 2.23
Log S: -4.67
Log(Vapor Pressure): -10.96
Melting Point: 179.74
pKa Acid: 5.21
pKa Basic: 6.82

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9735
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9068
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9003
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8993
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8931
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8892
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8864
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8662
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8639
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8622
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8616
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8377
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8362
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8322
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8320
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8304
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8293
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8195
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8131
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8079
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7965
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7947
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7909
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7895
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7867
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7851
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7850
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7826
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7770
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7767
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7756
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7663
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7608
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7536
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7494
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7491
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7385
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	4	0.7326
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7253
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7246
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7189
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7183
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7144
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7130
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7107
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7104
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7098
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7042
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7038
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7024
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7022
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7021

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