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1-O-p-hydroxybenzoyl-6-O-galloyl-bglucose

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

Canonical Smiles	Oc1ccc(cc1)C(=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
InChI	InChI=1S/C20H20O12/c21-10-3-1-8(2-4-10)19(29)32-20-17(27)16(26)15(25)13(31-20)7-30-18(28)9-5-11(22)14(24)12(23)6-9/h1-6,13,15-17,20-27H,7H2/t13-,15-,16+,17-,20+/m1/s1
InChIKey	BHSFXHMEMNALHW-RGCXKDKSSA-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]

Pubchem: 14428084

Zinc: ZINC000015251461

Nmrshiftdb2: 60026127

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 340.38 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 220.27 g/mol

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 206.24 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): -6.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.450
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.670
Plasma Protein Binding: 68.07
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: 13.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.790
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.890
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.160
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: -50.920
Rat (Acute): 2.080
Rat (Chronic Oral): 3.980
Fathead Minnow: 3.920
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: 595.620
Hydration Free Energy: -6.620
Log(D) at pH=7.4: 0.500
Log(P): 0.31
Log S: -3.82
Log(Vapor Pressure): -11.56
Melting Point: 198.65
pKa Acid: 5.7
pKa Basic: 4.82

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	0.9260
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9174
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9095
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9019
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8931
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8790
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8746
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8653
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8650
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8623
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8574
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8559
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8516
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8466
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8448
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8433
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8432
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8418
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8393
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8374
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8303
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8267
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8265
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8264
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8244
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8198
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8188
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8172
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8061
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8046
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8041
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8033
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8001
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8000
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7966
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7935
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7845
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7844
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7746
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7687
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7668
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7666
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7618
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7609
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7595
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7560
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7555
1,4-alpha-glucan branching enzyme GlgB	A7ZSW5	GLGB_ECO24	Escherichia coli O139:H28	3	0.7548
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7522
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7468
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7461
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7401
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7343
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7322
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.7302
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7299
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7298
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7276
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7263
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7252
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7233
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7217
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7210
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7193
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7183
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7173
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7156
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7151
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7146
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7133
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7128
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7075
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7070
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7051
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7043
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7021
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7020

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