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Quercetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)O)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15-,17-,18-,20+,21+,22+,23-,26-,27+/m1/s1
InChIKey	OTUCXMIQUNROBJ-LOOCNDHYSA-N
Formula	C₂₇H₃₀O₁₆
HBA	16
HBD	10
MW	610.52
Rotatable Bonds	6
TPSA	269.43
LogP	-2.04
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	610.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chrozophora obliqua	Euphorbiaceae	Plantae	316753
2	Randonia africana	Resedaceae	Plantae	415773

Showing of synonyms

Berrehal D, Khalfallah A, et al. (2010). Flavonoid glycosides from Randonia africana Coss. (Resedaceae). Biochemical Systematics and Ecology,2010,38(5),1007-1009. [View]
Mohamed KM (2001). Phenylpropanoid glucosides from Chrozophora obliqua. Phytochemistry,2001,58,615-618. [View] [PubMed]

Pubchem: 54169142

Zinc: ZINC000072131688

Nmrshiftdb2: 70002524

Chembl: CHEMBL1774171

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.53
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.420
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 9.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.780
Plasma Protein Binding: 73.83
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: 9.420
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.280
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.060
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.530
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: -13855.030
Rat (Acute): 2.230
Rat (Chronic Oral): 4.430
Fathead Minnow: 30.580
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: 496.770
Hydration Free Energy: -3.000
Log(D) at pH=7.4: -0.870
Log(P): -1.3
Log S: -4.68
Log(Vapor Pressure): -14.85
Melting Point: 224.45
pKa Acid: 3.27
pKa Basic: 7.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8955
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8955
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8509
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8509
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8446
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8446
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8439
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8439
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8327
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8327
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8255
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8255
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7945
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7945
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7751
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7751
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7631
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7631
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7565
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7565
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7535
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7535
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7485
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7485
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7404
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7404
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7345
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7345
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7261
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7261
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7221
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7221
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7179
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7179
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7135
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7135
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7132
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7132
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7098
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7098
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7088
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7088
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7066
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7066
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7051
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7051
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7044
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7044
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7029
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7029
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7013
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7013

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