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Quercetin-3-O-beta-D-glucopyranoside

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

Canonical Smiles	OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13?,15-,17?,18+,21+/m1/s1
InChIKey	OVSQVDMCBVZWGM-OBLDEXFVSA-N
Formula	C₂₁H₂₀O₁₂
HBA	12
HBD	8
MW	464.38
Rotatable Bonds	4
TPSA	210.51
LogP	-0.54
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	464.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Carissa edulis	Apocynaceae	Plantae	992661
2	Livistona australis	Arecaceae	Plantae	115491

Showing of synonyms

Kassem MES, Shoela S, et al. (2012). A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity. Natural Product Research,2012,26(15),1381-1387. [View] [PubMed]
Al-Youssef HM and Hassan WHB. (2014). Chemical constituents of Carissa edulis Vahl. Arabian Journal of Chemistry,2014,in press. [View]

Pubchem: 89718967

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 464.38 g/mol

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

Level: 1

Mol. Weight: 464.38 g/mol

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

Level: 1

Mol. Weight: 464.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 464.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 464.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 464.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.25
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.83
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.16

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 72.04
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: 13.22
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.92
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: -107.5
Rat (Acute): 2.42
Rat (Chronic Oral): 3.86
Fathead Minnow: 3.84
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 643.38
Hydration Free Energy: -4.69
Log(D) at pH=7.4: -0.12
Log(P): 0.59
Log S: -4.16
Log(Vapor Pressure): -11.56
Melting Point: 211.02
pKa Acid: 5.46
pKa Basic: 8.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9184
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9184
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9011
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9011
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8928
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8928
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8920
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8920
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8902
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8902
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8802
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8802
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8789
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8789
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8753
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8753
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8750
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8750
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8750
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8750
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8630
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8630
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8593
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8593
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8588
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8588
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8587
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8587
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8480
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8480
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8433
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8433
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8396
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8396
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8387
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8387
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8366
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8366
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8346
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8346
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8301
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8301
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8228
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8228
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8151
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8151
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8095
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8095
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8025
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8025
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7988
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7988
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7986
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7986
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7959
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7959
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7945
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7945
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7938
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7938
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7868
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7868
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7834
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7834
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7816
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7816
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7788
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7788
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7785
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7785
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7773
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7773
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7759
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7759
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7658
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7658
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7653
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7653
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7613
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7613
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7602
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7602
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7562
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7562
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7557
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7557
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7507
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7507
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7501
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7501
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7468
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7468
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7428
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7428
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7394
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7394
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7380
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7380
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7378
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7378
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7337
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7337
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7324
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7324
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7290
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7290
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7274
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7274
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7263
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7263
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7249
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7249
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7241
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7241
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7236
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7236
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7228
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7228
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7227
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7227
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7219
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7219
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7166
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7166
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7155
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7155
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7140
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7140
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7090
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7090
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7090
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7090
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7080
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7080
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7025
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7025
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7012
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7012

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