Gallotannin 1,2,3,6-tetra-O-galloyl-beta-D-glucose - Compound Card

Gallotannin 1,2,3,6-tetra-O-galloyl-beta-D-glucose

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Gallotannin 1,2,3,6-tetra-O-galloyl-beta-D-glucose

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Tannin
    • Subclass: Ellagitannin
Canonical Smiles O[C@@H]1C(COC(=O)c2cc(O)c(c(c2)O)O)O[C@H]([C@H](C1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C34H28O22/c35-14-1-10(2-15(36)23(14)43)30(48)52-9-22-27(47)28(54-31(49)11-3-16(37)24(44)17(38)4-11)29(55-32(50)12-5-18(39)25(45)19(40)6-12)34(53-22)56-33(51)13-7-20(41)26(46)21(42)8-13/h1-8,22,27-29,34-47H,9H2/t22?,27-,28?,29+,34+/m1/s1
InChIKey RATQVALKDAUZBW-FINXCBKKSA-N
Formula C34H28O22
HBA 22
HBD 13
MW 788.58
Rotatable Bonds 9
TPSA 377.42
LogP 0.7
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 56
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 788.11
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix aphylla Tamaricaceae Plantae 189786

Showing of synonyms

  • Orabi MA, Yoshimura M, et al. (2015). Ellagitannins, gallotannins, and gallo-ellagitannins from the galls of Tamarix aphylla. Fitoterapia,2015,104,55-63. [View] [PubMed]
Pubchem: 162939040
Nmrshiftdb2: 70060299

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2OC(COC(=O)c3ccccc3)CC(OC(=O)c4ccccc4)C2OC(=O)c5ccccc5

Level: 4

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCC(OC(=O)c3ccccc3)C(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)CC(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)C(CO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)CCOC2OC(=O)c4ccccc4

Level: 3

Mol. Weight: 788.58 g/mol

Structure

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

Level: 2

Mol. Weight: 788.58 g/mol

Structure

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

Level: 2

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(CCO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CC(OCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OCCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 788.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 788.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 788.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
12.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2419.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
15.44
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
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
12.31
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-54.61
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.51
Micronucleos
Toxic
NR-AhR
Toxic
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
-4389572.43
Rat (Acute)
2.42
Rat (Chronic Oral)
4.59
Fathead Minnow
5551.3
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
483237.73
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-0.29
Log(P)
0.81
Log S
-6.76
Log(Vapor Pressure)
-15971.72
Melting Point
312.4
pKa Acid
-86.48
pKa Basic
3.26
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 0.9280
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9280
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9096
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9096
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9088
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9088
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9021
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9021
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8998
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8998
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8868
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8868
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8784
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8784
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8671
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8671
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8518
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8518
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8506
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8506
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8493
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8493
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8477
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8477
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8442
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8442
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8440
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8440
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8398
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8398
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8358
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8358
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8321
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8321
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8244
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8244
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8210
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8210
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8182
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8182
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8080
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8080
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8062
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8062
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7947
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7947
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7940
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7940
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7911
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7911
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7868
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7868
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7858
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7858
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7775
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7775
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7678
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7666
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7666
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7562
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7562
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7489
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7489
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7488
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7488
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7343
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7343
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7334
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7334
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7333
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7333
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7331
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7331
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7307
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7307
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7296
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7296
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7291
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7291
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7275
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7275
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7251
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7251
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7235
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7235
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7232
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7232
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7219
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7219
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7183
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7183
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7158
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7158
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7128
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7128
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7109
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7109
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7106
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7106
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7106
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7106
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7075
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7075
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7055
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7055
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7043
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7043
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7029
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7029
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7011
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7011

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