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2-O-p-hydroxybenzoyl-6-O-galloyl-(alpha/beta)-4C1-glucopyranose

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	Oc1ccc(cc1)C(=O)OC1C(O)OC([C@H]([C@@H]1O)O)COC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C20H20O12/c21-10-3-1-8(2-4-10)19(28)32-17-16(26)15(25)13(31-20(17)29)7-30-18(27)9-5-11(22)14(24)12(23)6-9/h1-6,13,15-17,20-26,29H,7H2/t13?,15-,16+,17?,20?/m1/s1
InChIKey	OQZUBZJEVMCTGO-UHEQQFMISA-N
Formula	C₂₀H₂₀O₁₂
HBA	12
HBD	7
MW	452.37
Rotatable Bonds	5
TPSA	203.44
LogP	-0.67
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	452.1
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]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCC(CO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 452.37 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 452.37 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 452.37 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 452.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 452.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.82
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.480
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.66

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 34.3
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: 13.250
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.460
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.790
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.550
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: -49.550
Rat (Acute): 2.130
Rat (Chronic Oral): 4.040
Fathead Minnow: 4.010
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 578.880
Hydration Free Energy: -6.640
Log(D) at pH=7.4: 0.610
Log(P): -0.06
Log S: -3.76
Log(Vapor Pressure): -10.79
Melting Point: 196.63
pKa Acid: 5.88
pKa Basic: 4.48

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9263
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9197
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9110
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9019
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8854
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8813
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8804
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8802
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8790
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8733
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8711
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8687
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8650
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8639
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8591
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8539
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8522
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8477
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8474
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8474
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8468
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8464
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8420
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8368
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8329
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8303
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8288
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8260
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8200
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8136
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8131
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	4	0.8114
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8108
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8053
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8041
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7967
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7944
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7915
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7897
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7857
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7839
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7820
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7771
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7762
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7719
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7713
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7710
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7702
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7682
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7671
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.7652
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7648
Type II methyltransferase M.RsrI	P14751	MTR1_RHOSH	Cereibacter sphaeroides	4	0.7555
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7515
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7502
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7501
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7486
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7449
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7446
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7427
Serine/threonine-protein kinase RAD53	P22216	RAD53_YEAST	Saccharomyces cerevisiae	4	0.7413
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7413
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7413
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7389
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7380
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7360
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7357
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7330
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7327
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7304
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7282
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	4	0.7281
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7272
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7267
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7264
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7257
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7256
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7254
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7248
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7240
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7240
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7236
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7236
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7234
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7232
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7229
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7220
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7217
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7215
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7176
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7173
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7173
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7168
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7155
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7151
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7150
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7146
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7145
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7130
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7129
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7126
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7107
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7105
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7103
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7081
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7078
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7077
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7074
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7074
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	4	0.7071
Nitrogenase iron protein 1	P00459	NIFH1_AZOVI	Azotobacter vinelandii	3	0.7065
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7060
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7055
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7047
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7043
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7029
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7023
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7016
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7006

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