Tri-O-galloyl glucose - Compound Card

Tri-O-galloyl glucose

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Tri-O-galloyl glucose

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Simple Gallate
Canonical Smiles O[C@H]1[C@H](O)O[C@@H]([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/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(38)42-7-17-22(44-25(39)9-3-13(30)19(35)14(31)4-9)23(21(37)27(41)43-17)45-26(40)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-37,41H,7H2/t17-,21-,22-,23-,27-/m1/s1
InChIKey QNGJHYZWDAADHI-HDCOVYJKSA-N
Formula C27H24O18
HBA 18
HBD 11
MW 636.47
Rotatable Bonds 7
TPSA 310.66
LogP -0.28
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 636.1
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992

Showing of synonyms

  • Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]
Pubchem: 14188641
Nmrshiftdb2: 60026900

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 636.47 g/mol

Structure

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

Level: 2

Mol. Weight: 636.47 g/mol

Structure

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

Level: 2

Mol. Weight: 636.47 g/mol

Structure

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

Level: 2

Mol. Weight: 636.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 636.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 636.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 636.47 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 636.47 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 636.47 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.35
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
12.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
36.65
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
13.26
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.25
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.11
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
-22560.72
Rat (Acute)
2.39
Rat (Chronic Oral)
4.22
Fathead Minnow
48.03
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
478.49
Hydration Free Energy
-2.94
Log(D) at pH=7.4
0.56
Log(P)
0.02
Log S
-5.22
Log(Vapor Pressure)
-16.8
Melting Point
247.84
pKa Acid
6.79
pKa Basic
4.55
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 0.9261
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9261
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9093
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9093
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9078
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9078
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8999
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8999
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8990
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8990
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8700
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8700
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8681
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8506
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8506
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8486
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8486
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8467
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8467
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8441
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8441
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8437
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8437
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8433
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8433
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8398
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8398
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8336
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8336
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8330
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8330
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8239
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8239
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8236
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8236
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8221
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8221
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8205
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8205
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8135
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8134
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8134
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8132
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8132
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8104
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8104
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8092
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7968
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7968
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7959
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7959
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7764
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7764
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7744
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7744
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
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7722
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7722
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7690
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7690
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7686
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7686
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7603
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7603
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.7527
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.7527
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7505
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7505
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7454
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7454
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7402
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7390
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7390
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7328
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7328
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7319
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7319
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7311
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7311
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7307
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7307
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7298
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7298
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7297
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7297
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7288
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7288
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7234
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7234
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7222
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7222
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7207
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7207
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7201
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7201
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7189
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7189
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7182
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7182
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7154
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7154
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7151
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7151
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7150
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7150
GTPase KRas P01116 RASK_HUMAN Homo sapiens 4 0.7137
GTPase KRas P01116 RASK_HUMAN Homo sapiens 4 0.7137
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7113
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7113
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7103
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7103
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7099
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7099
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7095
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7095
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7093
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7093
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7081
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7081
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7080
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7080
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
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7063
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7063
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7053
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7053
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7043
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7043
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7034
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7034
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7022
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022

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