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Quercetin 3-rhamnoside

Family: Plantae - Leguminosae/Fabaceae
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-/m0/s1
InChIKey	OXGUCUVFOIWWQJ-XIMSSLRFSA-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	Curya pecan	Juglandaceae	Plantae	32201
2	Tephrosia vogelii	Leguminosae/Fabaceae	Plantae	1157238

Showing of synonyms

Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
Ishak MS, Ahmed AA, et al. (1980). Flavonol glycosides of Carya pecan. Phytochemistry,1980,19,2512-2513. [View]

Pubchem: 5359430

Zinc: ZINC000009147122

Chebi: 75863

Nmrshiftdb2: 60023815

Metabolights: MTBLC75863

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

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.66
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: 84.94
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: 14.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.64
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: 5.62
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: -62.23
Rat (Acute): 2.36
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: 625.02
Hydration Free Energy: -6.04
Log(D) at pH=7.4: 0.6
Log(P): 1.28
Log S: -4.13
Log(Vapor Pressure): -11.42
Melting Point: 206.16
pKa Acid: 4.67
pKa Basic: 7.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9762
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9762
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9368
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9368
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9050
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9050
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8978
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8978
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8926
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8926
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8684
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8684
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8546
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8546
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8483
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8483
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8475
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8475
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8429
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8429
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8410
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8410
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8376
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8376
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8311
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8311
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8205
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8205
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8139
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8139
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8095
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8095
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8078
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8078
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8058
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8058
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8019
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8019
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7982
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7982
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7954
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7954
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7948
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7948
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7946
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7946
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7944
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7944
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7938
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7938
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7928
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7928
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7797
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7797
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7793
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7793
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7787
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7787
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7771
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7771
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7761
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7761
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7740
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7740
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7687
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7687
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7686
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7686
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7666
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7666
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7640
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7640
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7628
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7628
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7596
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7596
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7538
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7538
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7430
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7430
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7386
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7386
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7383
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7383
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7366
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7366
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7365
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7365
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7354
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7354
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7301
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7301
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7295
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7295
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7285
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7285
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7282
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7282
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7240
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7240
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7171
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7171
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7162
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7162
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7154
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7154
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7152
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7152
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7138
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7138
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7104
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7104
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7097
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7097
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7046
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7046
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7040
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7040
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7025
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7025
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7015
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7015
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7013
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7013
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7009
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7009

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