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Quercetin 3-O-(6′′-O-galloyl)-beta-galactopyranoside

Family: Plantae - Melastomaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Pyranoside

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC(COC(=O)c2cc(O)c(c(c2)O)O)C(C(C1O)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
InChIKey	FMQQLXJREAGPHS-UHFFFAOYSA-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	Dissotis perkinsiae	Melastomaceae	Plantae	2015420

Showing of synonyms

Ndjateu F, Tsafack R, et al. (2014). Antimicrobial and antioxidant activities of extracts and ten compounds from three Cameroonian medicinal plants: Dissotis perkinsiae (Melastomaceae), Adenocarpus mannii (Fabaceae) and Barteria fistulosa (Passifloraceae). South African Journal of Botany, 2014, 91, 37-42. [View]

Pubchem: 14055723

Nmrshiftdb2: 60028471

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 616.48 g/mol

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

Level: 2

Mol. Weight: 616.48 g/mol

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

Level: 2

Mol. Weight: 616.48 g/mol

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

Level: 1

Mol. Weight: 616.48 g/mol

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

Level: 1

Mol. Weight: 616.48 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 616.48 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 616.48 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 616.48 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 616.48 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.67
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: 13.23

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 27.93
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: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.27
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.16
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: -21000.98
Rat (Acute): 2.44
Rat (Chronic Oral): 4.21
Fathead Minnow: 46.07
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: 484.1
Hydration Free Energy: -3.16
Log(D) at pH=7.4: 0.34
Log(P): 1.35
Log S: -5.07
Log(Vapor Pressure): -16.58
Melting Point: 232.05
pKa Acid: 5.04
pKa Basic: 8.37

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9753
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9338
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9012
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8997
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8982
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8936
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8886
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8858
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8826
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8745
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8720
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8707
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8678
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8657
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8620
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8586
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8517
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8490
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8484
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8463
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8444
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8434
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8433
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8423
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8398
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8384
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8371
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8365
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8302
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8274
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8179
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8140
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8123
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8098
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8086
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8081
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8051
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8044
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8027
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7998
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7947
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7942
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7932
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7919
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7918
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7877
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7872
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7845
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7801
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7800
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7765
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7758
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7718
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7714
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7656
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7648
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7633
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7629
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7598
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7564
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7557
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7497
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7475
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7428
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7391
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7352
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7325
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7273
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7259
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7249
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7227
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7210
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7197
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7192
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7189
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7187
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7186
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7152
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7141
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7132
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7131
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.7104
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7101
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7096
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7088
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7084
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7076
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7060
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7057
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7039
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7010
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7007
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7006
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7005
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7000

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