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Quercetin-3,7-di-O-alpha-rhamnopyranoside

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	O[C@@H]1[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)c2ccc(c(c2)O)O)O[C@@H]([C@H]([C@@H]1O)O)C
InChI	InChI=1S/C27H30O15/c1-8-17(31)20(34)22(36)26(38-8)40-11-6-14(30)16-15(7-11)41-24(10-3-4-12(28)13(29)5-10)25(19(16)33)42-27-23(37)21(35)18(32)9(2)39-27/h3-9,17-18,20-23,26-32,34-37H,1-2H3/t8-,9-,17-,18-,20+,21+,22+,23+,26-,27-/m1/s1
InChIKey	GXLQUHPXGLZNGE-XRFUJASSSA-N
Formula	C₂₇H₃₀O₁₅
HBA	15
HBD	9
MW	594.52
Rotatable Bonds	5
TPSA	249.2
LogP	-1.01
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	594.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Randonia africana	Resedaceae	Plantae	415773
2	Tephrosia purpurea	Leguminosae/Fabaceae	Plantae	228354

Showing of synonyms

Kassem M.E.S, Sharaf M, et al. (2006). Bioactive Flavonoids from Tephrosia purpurea. Natural product communications, 2006, 1(11),. [View]
Berrehal D, Khalfallah A, et al. (2010). Flavonoid glycosides from Randonia africana Coss. (Resedaceae). Biochemical Systematics and Ecology,2010,38(5),1007-1009. [View]

Pubchem: 134734045

Nmrshiftdb2: 70131642

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.41
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 5.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 80.17
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: 10.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.99
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.04
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.66
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: -8166.88
Rat (Acute): 2.26
Rat (Chronic Oral): 4.27
Fathead Minnow: 18.57
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: 516.67
Hydration Free Energy: -3.12
Log(D) at pH=7.4: -0.21
Log(P): -0.49
Log S: -4.87
Log(Vapor Pressure): -12.4
Melting Point: 230.11
pKa Acid: 4.02
pKa Basic: 6.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8784
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8784
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8716
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8716
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8650
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8650
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8316
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8316
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8116
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8116
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8088
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8088
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8021
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8021
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7994
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7994
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7695
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7695
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7615
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7615
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7465
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7465
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7442
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7442
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7409
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7409
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7329
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7329
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7299
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7299
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7290
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7290
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7280
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7280
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7271
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7271
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7262
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7262
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7219
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7219
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7212
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7212
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7188
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7188
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7096
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7096
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7001
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7001

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