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Quercetin 3-alpha-L-rhamnopyranoside

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21+/m1/s1
InChIKey	OXGUCUVFOIWWQJ-AIRRAIBWSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	7
MW	448.38
Rotatable Bonds	3
TPSA	190.28
LogP	0.49
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Embelia schimperi	Primulaceae	Plantae	2595069

Showing of synonyms

Hussein G, Miyashiro H, et al. (2000). Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. Phytotherapy Research,2000,14(7),510-516. [View] [PubMed]

Pubchem: 40486293

Zinc: ZINC000004416342

Nmrshiftdb2: 60027062

Chembl: CHEMBL250696

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

Antiviral

Absorption

Caco-2 (logPapp): -6.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 84.91
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: -1.66
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.21
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.63
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: -62.19
Rat (Acute): 2.37
Rat (Chronic Oral): 3.96
Fathead Minnow: 3.71
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: 625.64
Hydration Free Energy: -6.05
Log(D) at pH=7.4: 0.59
Log(P): 1.24
Log S: -4.14
Log(Vapor Pressure): -11.41
Melting Point: 207.54
pKa Acid: 4.65
pKa Basic: 7.46

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9765
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9765
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8990
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8990
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8957
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8957
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8932
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8932
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8778
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8778
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8728
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8728
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8591
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8591
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8519
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8519
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8497
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8497
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8342
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8342
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8299
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8299
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8238
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8238
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8219
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8219
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8207
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8207
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8204
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8204
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8132
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8132
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8108
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8108
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8098
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8098
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8095
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8095
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7968
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7968
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7942
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7942
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7940
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7940
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7876
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7876
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7840
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7840
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7838
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7838
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7750
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7750
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7742
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7742
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7727
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7727
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7639
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7639
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7629
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7629
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7614
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7614
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7607
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7607
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7536
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7536
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7471
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7471
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7392
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7392
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7372
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7372
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7323
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7323
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7313
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7313
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7299
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7299
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7281
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7281
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7227
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7227
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7203
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7203
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7168
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7168
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7126
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7126
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7109
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7109
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7091
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7091
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7090
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7090
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7054
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7054
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7036
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7036
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7035
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7035
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	4	0.7029
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	4	0.7029
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	5	0.7016
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	5	0.7016
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7012
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7012
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7008
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7008
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7001
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7001

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