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3,3',4-trimethoxyellagic acid-4'-glucoside

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc3c(=O)oc4c5c3c(c2OC)oc(=O)c5cc(c4OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C23H22O13/c1-30-9-4-7-12-13-8(22(29)35-19(12)17(9)31-2)5-10(18(32-3)20(13)36-21(7)28)33-23-16(27)15(26)14(25)11(6-24)34-23/h4-5,11,14-16,23-27H,6H2,1-3H3/t11-,14-,15+,16-,23-/m1/s1
InChIKey	RKFCDGOVCBYSEW-AUUKWEANSA-N
Formula	C₂₃H₂₂O₁₃
HBA	13
HBD	4
MW	506.42
Rotatable Bonds	6
TPSA	187.49
LogP	-0.31
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	506.11
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Psidium guajava	Myrtaceae	Plantae	120290
2	Gunnera perpensa	Gunneraceae	Plantae	138603

Showing of synonyms

Salib JY, Michael HN (2004). Cytotoxic phenylethanol glycosides from Psidium guaijava seeds. Phytochemistry,2004,65(14),2091-2093. [View] [PubMed]
Khan F, Peter XK, et al. (2004). Venusol from Gunnera perpensa: structural and activity studies. Phytochemistry, 2004, 65(8), 1117–1121. [View]

Pubchem: 44567156

Zinc: ZINC000044387717

Nmrshiftdb2: 60026899

Chembl: CHEMBL463271

No compound-protein relationship available.

SMILES: c12c3c4c(=O)oc2cc(OC5CCCCO5)cc1c(=O)oc3ccc4

Level: 1

Mol. Weight: 506.42 g/mol

SMILES: c12c3c4c(=O)oc2cccc1c(=O)oc3ccc4

Level: 0

Mol. Weight: 506.42 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 506.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.09
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.820
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.28

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.270
Plasma Protein Binding: 79.03
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: 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: 2.290
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.310
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.060
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.490
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -690.300
Rat (Acute): 2.490
Rat (Chronic Oral): 3.710
Fathead Minnow: 5.190
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 579.610
Hydration Free Energy: -2.840
Log(D) at pH=7.4: 2.220
Log(P): -0.93
Log S: -3.75
Log(Vapor Pressure): -10.36
Melting Point: 191.09
pKa Acid: 5.77
pKa Basic: 1.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9226
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9226
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9003
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9003
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8853
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8853
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8818
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8818
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8815
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8815
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8642
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8642
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8588
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8588
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8504
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8504
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8382
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8382
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8121
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8121
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7991
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7991
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7972
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7972
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7836
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7836
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7821
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7821
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7787
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7787
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7617
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7617
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7555
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7555
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7548
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7548
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7517
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7517
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7487
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7487
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7457
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7457
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7444
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7444
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7438
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7438
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7392
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7392
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7369
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7369
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7364
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7364
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7340
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7340
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7288
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7288
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7280
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7280
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7272
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7272
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7249
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7249
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7238
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7238
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7232
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7232
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7171
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7171
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7148
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7148
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7143
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7143
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7131
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7131
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7127
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7127
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7108
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7108
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7096
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7096
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7084
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7084
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7083
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7083
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7062
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7062
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7030
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7030
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7025
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7025
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7009
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7009

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