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Quercetin-3-O-beta-D-xylopyranoside

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15+,17-,20+/m1/s1
InChIKey	PZZRDJXEMZMZFD-BWYUNELBSA-N
Formula	C₂₀H₁₈O₁₁
HBA	11
HBD	7
MW	434.35
Rotatable Bonds	3
TPSA	190.28
LogP	0.1
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	434.08
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Elaeophorbia drupifera	Euphorbiaceae	Plantae	212879
2	Syzygium cumini	Myrtaceae	Plantae	—

Showing of synonyms

Voukeng IK, Nganou BK, et al. (2017). Antibacterial activities of the methanol extract, fractions and compounds from Elaeophorbia drupifera (Thonn.) Stapf. (Euphorbiaceae).. BMC complementary and alternative medicine,2017, 17(1), 28. [View] [PubMed]
Eldin Elhawary S.S, Elmotyam A.K.E, et al. (2022). Cytotoxic and anti-diabetic potential, metabolic profiling and insilico studies of Syzygium cumini (L.) Skeels belonging to family Myrtaceae. Natural product research,2022, 36(4), 1026-1030. [View] [PubMed]

Pubchem: 5320861

Gnps: CCMSLIB00000081774

Zinc: ZINC000025763680

Chebi: 69456

Nmrshiftdb2: 60026145

Metabolights: MTBLC69456

Chembl: CHEMBL488198

CPRiL: 446174

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

Level: 2

Mol. Weight: 434.35 g/mol

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

Level: 1

Mol. Weight: 434.35 g/mol

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

Level: 1

Mol. Weight: 434.35 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 434.35 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.35 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.34
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.67
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 85.2
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 13.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.94
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.17
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.63
Micronucleos: Toxic
NR-AhR: Toxic
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: -42.13
Rat (Acute): 2.45
Rat (Chronic Oral): 3.67
Fathead Minnow: 3.87
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 612.14
Hydration Free Energy: -7.62
Log(D) at pH=7.4: 0.4
Log(P): 0.94
Log S: -4.15
Log(Vapor Pressure): -10.85
Melting Point: 230.27
pKa Acid: 5.91
pKa Basic: 7.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9165
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9144
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8998
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8913
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8830
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8691
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8688
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8616
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8561
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8555
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8549
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8507
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8488
6,7-dimethyl-8-ribityllumazine synthase	Q9UUB1	RIB4_SCHPO	Schizosaccharomyces pombe	6	0.8458
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8429
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8401
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8356
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8346
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8280
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8242
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8168
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8092
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8088
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8066
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8049
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8027
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8018
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7972
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7959
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7907
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7896
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7867
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7858
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7850
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7838
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7779
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7763
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7680
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7646
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7613
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7556
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7544
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7543
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7520
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7500
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7491
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7487
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7483
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7472
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7465
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7457
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7445
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7431
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7399
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7395
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7385
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7381
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7329
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7319
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7273
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7235
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7201
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7193
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7190
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7188
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7179
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7172
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7160
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7147
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7140
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7105
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7105
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7096
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7096
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7076
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7063
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7060
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7059
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7055
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7048
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7036
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7030
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7025
Protein kinase, putative	Q4YRR5	Q4YRR5_PLABA	Plasmodium berghei	4	0.7009
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7003

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