1,6-di-O-galloyl-beta-D-glucose - Compound Card

1,6-di-O-galloyl-beta-D-glucose

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1,6-di-O-galloyl-beta-D-glucose

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Gallic Acid Derivative
Canonical Smiles OC1C(COC(=O)c2cc(O)c(c(c2)O)O)OC(C(C1O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C20H20O14/c21-8-1-6(2-9(22)13(8)25)18(30)32-5-12-15(27)16(28)17(29)20(33-12)34-19(31)7-3-10(23)14(26)11(24)4-7/h1-4,12,15-17,20-29H,5H2
InChIKey LYGRISUQIZNHGM-UHFFFAOYSA-N
Formula C20H20O14
HBA 14
HBD 9
MW 484.37
Rotatable Bonds 5
TPSA 243.9
LogP -1.26
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 484.09
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Phyllanthus emblica Euphorbiaceae Plantae 296036

Showing of synonyms

  • El-Mekkawy S, Meselhy MR, et al. (1995). Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase. Chemical and Pharmaceutical Bulletin,1995,43(4),641-648. [View] [PubMed]
Pubchem: 3332212
Nmrshiftdb2: 60075537

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 484.37 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 484.37 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 484.37 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 484.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.37 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-6.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.94
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
5.61
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
13.19
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.54
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.77
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.72
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
-108.38
Rat (Acute)
2.02
Rat (Chronic Oral)
4.1
Fathead Minnow
3.51
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
662.42
Hydration Free Energy
-4.26
Log(D) at pH=7.4
-0.81
Log(P)
-0.66
Log S
-3.78
Log(Vapor Pressure)
-12.88
Melting Point
200.84
pKa Acid
5.07
pKa Basic
7.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9271
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9256
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9256
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9016
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9016
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8824
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8824
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8780
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8780
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8698
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8698
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8667
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8667
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8639
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8639
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8573
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8573
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 0.8486
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8486
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8464
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8464
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8441
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8441
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8389
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8389
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8318
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8318
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8300
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8300
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8210
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8210
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8186
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8186
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8163
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8163
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8156
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8156
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8060
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8060
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8049
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8049
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8047
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8047
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8041
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8041
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8040
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8040
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7967
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7967
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7918
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7918
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7880
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7880
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7789
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7789
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7777
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7777
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7770
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7770
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7729
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7729
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7727
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7727
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7703
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7703
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7668
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7668
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7605
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7605
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7564
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7564
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7563
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7563
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7513
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7513
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7494
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7494
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7487
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7487
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7465
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7465
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7424
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7424
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7415
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7415
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.7404
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.7404
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7353
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7345
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7345
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7310
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7310
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7285
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7285
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7263
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7263
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7240
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7240
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
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
Glucanase B7X9Z2 B7X9Z2_COPCI Coprinopsis cinerea 4 0.7229
Glucanase B7X9Z2 B7X9Z2_COPCI Coprinopsis cinerea 4 0.7229
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7227
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7227
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7220
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7220
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7214
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7214
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7211
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7211
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7175
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7175
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7171
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7171
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7171
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7171
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7164
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7164
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7140
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7140
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7132
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7132
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7126
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7126
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7118
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7118
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7114
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7114
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7101
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7101
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7085
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7085
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7074
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7074
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7066
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7066
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7056
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7056
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7035
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7035
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7034
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7034
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7029
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7029
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7026
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7026
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7025
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7025
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7017
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7017
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7012
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7012

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