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Eugenol 5-O-beta-(6'-O-galloylglucopyranoside)

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

Canonical Smiles	C=CCc1cc(O[C@@H]2OC(COC(=O)c3cc(O)c(c(c3)O)O)[C@H]([C@@H](C2O)O)O)c(c(c1)OC)O
InChI	InChI=1S/C23H26O12/c1-3-4-10-5-14(32-2)18(27)15(6-10)34-23-21(30)20(29)19(28)16(35-23)9-33-22(31)11-7-12(24)17(26)13(25)8-11/h3,5-8,16,19-21,23-30H,1,4,9H2,2H3/t16?,19-,20+,21?,23-/m1/s1
InChIKey	LFQREKVEOMIWQF-RUFAMXIPSA-N
Formula	C₂₃H₂₆O₁₂
HBA	12
HBD	7
MW	494.45
Rotatable Bonds	8
TPSA	195.6
LogP	0.29
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	494.14
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)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 494.45 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 494.45 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 494.45 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 494.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 494.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.88
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.48
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.49

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.74
Plasma Protein Binding: 50.63
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: 13.03
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.18
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.78
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.12
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: -216.15
Rat (Acute): 2.09
Rat (Chronic Oral): 4.01
Fathead Minnow: 4.05
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: 594.12
Hydration Free Energy: -3.67
Log(D) at pH=7.4: 0.78
Log(P): 0.76
Log S: -4.53
Log(Vapor Pressure): -11.65
Melting Point: 165.01
pKa Acid: 5.57
pKa Basic: 5.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9427
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9311
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9118
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9116
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9112
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9052
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9001
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8953
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8896
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8875
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8835
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8782
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8764
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8734
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8678
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8565
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8548
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8522
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8477
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8449
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.8397
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8348
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	4	0.8341
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8340
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8328
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8311
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8286
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8245
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8163
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.8077
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8074
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8054
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8051
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8046
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8041
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8011
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7961
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7897
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7866
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7849
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7823
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7795
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7789
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7784
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	5	0.7783
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7780
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7759
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7679
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7677
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7675
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7671
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7664
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7648
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7585
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7576
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7559
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7540
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7538
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7515
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7508
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7499
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7498
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7496
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7492
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7489
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7487
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7487
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7463
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7463
Glutaminyl-peptide cyclotransferase	Q16769	QPCT_HUMAN	Homo sapiens	4	0.7460
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7446
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7440
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7415
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7411
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7382
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7377
Serine/threonine-protein kinase PAK 4	O96013	PAK4_HUMAN	Homo sapiens	4	0.7372
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7357
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7329
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7325
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7325
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7291
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7281
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7275
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7274
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7253
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7249
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7240
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7235
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7233
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7231
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7231
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7213
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7209
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7177
N-lysine methyltransferase KMT5A	Q9NQR1	KMT5A_HUMAN	Homo sapiens	4	0.7170
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7144
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7121
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7120
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7120
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7101
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7081
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7078
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7059
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7058
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7053
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7041
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7040
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7028
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7027
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7021
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7021
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7019
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7005

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