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Quercetin 3-O-xyloside

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC[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-DUYPVGENSA-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	Cynanchum acutum	Apocynaceae	Plantae	185024
2	Senecio angulatus	Asteraceae	Plantae	189229

Showing of synonyms

Heneidak S, Grayer RJ, et al. (2006). Flavonoid glycosides from Egyptian species of the tribe Asclepiadeae (Apocynaceae, subfamily Asclepiadoideae). Biochemical Systematics and Ecology,2006,34(7),575-584. [View]
Bousetla A, Keskinkaya H.B, et al. (2023). LC-ESI/MS-phytochemical profiling with antioxidant and antiacetylcholinesterase activities of Algerian Senecio angulatus L.f. extracts. Natural product research, 2023, 37(1), 123-129. [View] [PubMed]

Pubchem: 5320863

Cas: 549-32-6

Gnps: CCMSLIB00005756328

Nmrshiftdb2: 60031637

Comptox: DTXSID10415782

CPRiL: 421981

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

No bioactivities available.

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: 1.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 80.37
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: -1.93
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: 4.62
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: -41.93
Rat (Acute): 2.45
Rat (Chronic Oral): 3.68
Fathead Minnow: 3.89
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: 611.16
Hydration Free Energy: -7.63
Log(D) at pH=7.4: 0.39
Log(P): 0.82
Log S: -4.13
Log(Vapor Pressure): -10.7
Melting Point: 227.52
pKa Acid: 5.91
pKa Basic: 7.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9461
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9461
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8993
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8993
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8974
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8974
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8925
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8925
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8828
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8828
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8802
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8802
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8723
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8723
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8659
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8659
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8621
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8621
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8618
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8618
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8611
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8611
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8546
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8546
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8525
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8525
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8500
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8500
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8344
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8344
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8315
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8315
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8297
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8297
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8270
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8270
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8167
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8167
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8158
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8158
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8102
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8102
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8083
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8083
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8060
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8060
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8045
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8045
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8045
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8045
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8028
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8028
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7999
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7999
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7999
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7999
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7993
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7993
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7984
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7984
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7878
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7878
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7857
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7857
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7809
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7809
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7807
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7807
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7726
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7726
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7721
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7721
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7693
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7693
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7689
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7689
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7652
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7652
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7632
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7632
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7610
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7610
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7609
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7609
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7583
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7583
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7545
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7545
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7530
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7530
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7516
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7516
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7489
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7489
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7487
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7487
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7468
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7468
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7466
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7466
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7462
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7462
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7462
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7462
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7442
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7442
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7350
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7350
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7323
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7323
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7322
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7322
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7308
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7308
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7298
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7298
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7278
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7278
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7238
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7238
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7219
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7219
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7217
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7217
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7196
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7196
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7181
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7181
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7139
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7139
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7129
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7129
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7118
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7118
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7105
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7105
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7084
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7084
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7079
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7079
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7036
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7036
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7032
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7032
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7021
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7021
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7009
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7009
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7005
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7005
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7002
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7002

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