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2,6-di-O-galloyl glucose

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Tannin
- Subclass: Hydrolyzable Tannin

Canonical Smiles	O=C[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c1cc(O)c(c(c1)O)O)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C20H20O14/c21-5-14(34-20(32)8-3-11(24)16(28)12(25)4-8)18(30)17(29)13(26)6-33-19(31)7-1-9(22)15(27)10(23)2-7/h1-5,13-14,17-18,22-30H,6H2/t13-,14+,17-,18-/m1/s1
InChIKey	NKUMECHNWXWONJ-LTCOOKNTSA-N
Formula	C₂₀H₂₀O₁₄
HBA	14
HBD	9
MW	484.37
Rotatable Bonds	9
TPSA	251.74
LogP	-1.42
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	484.09
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Melaleuca ericifolia	Myrtaceae	Plantae	73757

Showing of synonyms

Hussein S.A, Hashim A.N, et al. (2007). Ericifolin: An eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia. Phytochemistry,2007, 68(10), 1464-70. [View] [PubMed]

Pubchem: 54116668

Cas: 94356-20-4

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCCCCCOC(=O)c2ccccc2

Level: 1

Mol. Weight: 484.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.81
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.89
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.29
Plasma Protein Binding: 42.75
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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.27
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.08
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.47
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: -85.88
Rat (Acute): 2.1
Rat (Chronic Oral): 3.9
Fathead Minnow: 3.69
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: 672.36
Hydration Free Energy: -4.82
Log(D) at pH=7.4: -0.83
Log(P): -0.99
Log S: -3.63
Log(Vapor Pressure): -13.09
Melting Point: 200.99
pKa Acid: 4.4
pKa Basic: 6.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.9405
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9275
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9034
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9015
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8821
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8697
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8693
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8693
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8644
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8618
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8559
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8537
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8525
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8509
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8461
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8444
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8442
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8438
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8388
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8371
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8334
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8281
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8259
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8189
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8156
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8151
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8125
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8096
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8072
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8050
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8027
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.8015
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7990
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7967
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7960
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7959
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7924
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7907
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7870
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7866
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	4	0.7858
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	5	0.7851
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7837
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7796
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7782
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7763
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7712
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7679
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7624
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7595
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7567
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7563
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7472
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7460
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7450
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7435
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7427
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7420
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7413
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7409
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7392
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7376
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7338
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7320
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7319
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7313
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7310
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7308
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7300
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7266
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7263
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7262
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7260
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7255
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7251
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7240
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7240
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7225
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7209
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7200
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7184
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7177
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7175
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7169
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7160
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7136
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7135
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7134
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7130
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7117
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7111
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7102
Mitogen-activated protein kinase FUS3	P16892	FUS3_YEAST	Saccharomyces cerevisiae	4	0.7100
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	4	0.7096
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7086
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7071
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7060
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7047
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7046
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7037
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.7037
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7020
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7019
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7015

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