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Quercetin-3-O-beta- 6''-galloylglucoside

Family: Myrtaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@H]1O[C@@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C28H24O16/c29-11-6-14(32)19-17(7-11)42-25(9-1-2-12(30)13(31)3-9)26(22(19)37)44-28-24(39)23(38)21(36)18(43-28)8-41-27(40)10-4-15(33)20(35)16(34)5-10/h1-7,18,21,23-24,28-36,38-39H,8H2/t18-,21-,23+,24-,28+/m0/s1
InChIKey	FMQQLXJREAGPHS-IQCXILKMSA-N
Formula	C₂₈H₂₄O₁₆
HBA	16
HBD	10
MW	616.48
Rotatable Bonds	6
TPSA	277.27
LogP	0.44
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	616.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eugenia edulis	Myrtaceae	Plantae	2729927

Showing of synonyms

Hussein S.A, Hashem A.N, et al. (2003). Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry, 2003, 64(4), 883-9. [View] [PubMed]

Pubchem: 154831695

Zinc: ZINC000095914697

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 456.49 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 380.4 g/mol

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

Level: 2

Mol. Weight: 322.36 g/mol

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

Level: 1

Mol. Weight: 246.26 g/mol

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

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 220.27 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.68
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 13.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 67.53
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: 13.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.69
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.17
Micronucleos: Toxic
NR-AhR: Toxic
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: -21004.32
Rat (Acute): 2.45
Rat (Chronic Oral): 4.19
Fathead Minnow: 45.98
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 488.41
Hydration Free Energy: -3.16
Log(D) at pH=7.4: 0.41
Log(P): 1.28
Log S: -5.14
Log(Vapor Pressure): -17.15
Melting Point: 232.65
pKa Acid: 5.03
pKa Basic: 8.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9752
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9305
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9113
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9105
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9093
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9000
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8996
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8932
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8919
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8871
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8848
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8809
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8724
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8523
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8509
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8497
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8457
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8455
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8446
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8418
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8379
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8368
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8343
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8266
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8222
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8218
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8175
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8138
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8137
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8109
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8078
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8077
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8029
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8017
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8005
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7975
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7938
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7900
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7889
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7882
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7870
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7851
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7839
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7826
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7790
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7783
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7780
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7760
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7743
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7734
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7726
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7719
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7642
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7635
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7627
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7616
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7611
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7593
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7578
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7561
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7468
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7461
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7456
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7437
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7435
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7414
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7406
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7388
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7379
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7378
chitinase	B0Y2Y2	B0Y2Y2_ASPFC	Aspergillus fumigatus	4	0.7352
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7350
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7346
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7346
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7322
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7315
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7314
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7314
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7291
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7286
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7264
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7257
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7255
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7252
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7231
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7200
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7183
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7181
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7152
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7148
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7140
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7138
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7123
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7111
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7105
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7102
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7094
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7080
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7071
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7071
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7070
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7049
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7031
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7029

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