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Quercetin-3-O-[6'''-alpha-L-rhamnosyl-6''-beta-D-glucosyl]-beta-D-glucoside

Family: Plantae - Capparaceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)OC1O[C@H](CO[C@@H]2O[C@H](CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C33H40O21/c1-9-19(38)23(42)26(45)31(50-9)48-7-16-20(39)24(43)27(46)32(52-16)49-8-17-21(40)25(44)28(47)33(53-17)54-30-22(41)18-14(37)5-11(34)6-15(18)51-29(30)10-2-3-12(35)13(36)4-10/h2-6,9,16-17,19-21,23-28,31-40,42-47H,7-8H2,1H3/t9-,16+,17+,19-,20+,21+,23+,24-,25-,26+,27+,28+,31+,32+,33?/m0/s1
InChIKey	SYFFHZSTXDTJOS-OQNXJHIZSA-N
Formula	C₃₃H₄₀O₂₁
HBA	21
HBD	13
MW	772.66
Rotatable Bonds	9
TPSA	348.58
LogP	-3.86
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	772.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Capparis spinosa	Capparaceae	Plantae	65558

Showing of synonyms

Sharaf M, El-Ansari MA, et al. (2000). Quercetin triglycoside from Capparis spinosa. Fitoterapia,2000,71(1),46-49. [View] [PubMed]

Pubchem: 163090030

Nmrshiftdb2: 70054180

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 772.66 g/mol

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

Level: 2

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCCO3

Level: 2

Mol. Weight: 772.66 g/mol

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

Level: 1

Mol. Weight: 772.66 g/mol

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

Level: 1

Mol. Weight: 772.66 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 772.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 772.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 772.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4.64
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1470.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.63
Plasma Protein Binding: 48.35
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: 10.07
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -33.7
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.79
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.18
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: -2664047.14
Rat (Acute): 2.23
Rat (Chronic Oral): 4.91
Fathead Minnow: 3370.83
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: 292226.23
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -2.27
Log(P): -1.64
Log S: -4.48
Log(Vapor Pressure): -9587.89
Melting Point: 227.05
pKa Acid: -37.34
pKa Basic: 9.04

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9768
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9768
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9265
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9265
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9092
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9092
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8958
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8958
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8814
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8814
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8742
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8742
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8734
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8734
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8730
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8730
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8581
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8581
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8534
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8534
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8512
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8512
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8509
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8509
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8372
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8372
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8241
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8241
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8167
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8167
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8151
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8151
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8052
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8052
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8045
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8045
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8037
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8037
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7914
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7914
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7899
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7899
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7877
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7877
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7865
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7865
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7819
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7819
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7809
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7809
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7730
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7730
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7715
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7715
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7706
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7706
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7698
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7698
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7599
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7599
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7577
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7577
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7552
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7552
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7423
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7423
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7305
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7305
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7300
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7300
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7220
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7220
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7100
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7100
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7083
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7083
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7073
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7073
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7009
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7009

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