2,3,4,6-tetragalloyl glucose - Compound Card

2,3,4,6-tetragalloyl glucose

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2,3,4,6-tetragalloyl glucose

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Tannin
    • Subclass: Tannin
Canonical Smiles O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1[C@H](OC[C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)COC(=O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C34H28O21/c35-15-1-11(2-16(36)25(15)43)31(47)52-9-23-29(54-33(49)13-5-19(39)27(45)20(40)6-13)30(55-34(50)14-7-21(41)28(46)22(42)8-14)24(10-51-23)53-32(48)12-3-17(37)26(44)18(38)4-12/h1-8,23-24,29-30,35-46H,9-10H2/t23-,24+,29-,30-/m1/s1
InChIKey PTFPGFMNLAMIJY-XSHKJCDBSA-N
Formula C34H28O21
HBA 21
HBD 12
MW 772.58
Rotatable Bonds 9
TPSA 357.19
LogP 1.39
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 55
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 772.11
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia arjuna Combretaceae Plantae 172200

Showing of synonyms

  • Kandil FE, Nassar MI (1998). A tannin anti-cancer promotor from Terminalia arjuna. Phytochemistry,1998,47(8),1567-1568. [View] [PubMed]
Pubchem: 11520609
Nmrshiftdb2: 60033232

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)C(CO2)OC(=O)c5ccccc5

Level: 4

Mol. Weight: 772.58 g/mol

Structure

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

Level: 3

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CC(CO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(CCO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)COCC2OC(=O)c4ccccc4

Level: 3

Mol. Weight: 772.58 g/mol

Structure

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

Level: 2

Mol. Weight: 772.58 g/mol

Structure

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

Level: 2

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2C(CCCO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CC(COC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 772.58 g/mol

Structure

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

Level: 2

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 772.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 772.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
6.49
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1647.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
31.46
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
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
13.02
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-36.47
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.38
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
-2989086.31
Rat (Acute)
2.53
Rat (Chronic Oral)
4.23
Fathead Minnow
3783.3
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
326004.34
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.66
Log(P)
0.87
Log S
-6.5
Log(Vapor Pressure)
-10803.23
Melting Point
347.57
pKa Acid
-47.0
pKa Basic
1.26
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 0.9246
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9246
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9068
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9068
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9045
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9045
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8720
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8720
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8672
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8672
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8642
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8642
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8545
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8545
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
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8492
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8492
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8459
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8459
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8414
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8414
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8344
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8344
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8263
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8263
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8248
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8248
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8189
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8189
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8140
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8140
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8072
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8072
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7958
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7958
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7941
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7941
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7940
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7940
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7907
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7907
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7822
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7822
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7818
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7818
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7817
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7817
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7739
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7739
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7678
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7596
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7596
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7513
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7513
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7413
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7413
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 4 0.7384
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 4 0.7384
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7373
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7373
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7347
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7347
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7287
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7287
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7263
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7263
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7220
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7220
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7215
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7215
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7160
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7160
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7110
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7110
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7102
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7102
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7094
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7094
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7076
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7068
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7068
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7055
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7055
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7011
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7011
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7007
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7007

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