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1,3,6-tri-O-galloyl-beta-D-glucopyranoside
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Tannin
- Subclass: Hydrolyzable Tannin
| Canonical Smiles | OC1C(COC(=O)c2cc(O)c(c(c2)O)O)OC(C(C1OC(=O)c1cc(O)c(c(c1)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)23(44-25(40)9-3-13(30)19(35)14(31)4-9)22(38)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2 |
| InChIKey | RNKMOGIPOMVCHO-UHFFFAOYSA-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 | Joannesia princeps | Euphorbiaceae | Plantae | 179690 |
Showing of synonyms
1,3,6-tri-O-galloyl-beta-D-glucopyranoside
1,3,6-tris-o-(3,4,5-trihydroxybenzoyl)hexopyranose
[3,5-dihydroxy-4,6-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
NSC-69861
CHEMBL5193262
SCHEMBL15302682
SCHEMBL19619865
DTXSID20860224
NSC69861
GLUCOPYRANOSE,3,6-TRIGALLATE
NS00125054
1,3,6-Trigalloylglucose
1,3,6-Tri-O-galloyl-beta-D-glucopyranose
- Camero C, Temraz A, et al. (2017). Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves.. Biochemical Systematics and Ecology, 2017, 70, 69-72. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)CC(O2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OCC2CC(CCO2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OC2CC(OCC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OCC2CCCCO2
Level: 1
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OC2CCOCC2
Level: 1
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1C(=O)OC2CCCCO2
Level: 1
Mol. Weight: 636.47 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 636.47 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 636.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.76
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.47
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 12.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.45
- Plasma Protein Binding
- 2.82
- 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
- 12.82
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.78
- 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
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.06
- 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
- -22698.99
- Rat (Acute)
- 2.3
- Rat (Chronic Oral)
- 4.23
- Fathead Minnow
- 47.72
- 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
- 443.11
- Hydration Free Energy
- -2.99
- Log(D) at pH=7.4
- -0.22
- Log(P)
- -0.03
- Log S
- -5.41
- Log(Vapor Pressure)
- -16.3
- Melting Point
- 249.81
- pKa Acid
- 5.7
- pKa Basic
- 5.44
| 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 | 0.9263 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9173 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9019 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8948 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8881 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8875 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8862 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8673 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8594 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8527 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8519 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8518 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8502 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 4 | 0.8501 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8435 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8391 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8356 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8349 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8346 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8263 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.8204 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8097 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.8043 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 4 | 0.7910 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7892 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 4 | 0.7795 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7770 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7767 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 4 | 0.7752 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7715 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7696 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 4 | 0.7641 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 4 | 0.7626 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7523 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 4 | 0.7514 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7484 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7429 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7408 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7289 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 4 | 0.7286 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7282 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 4 | 0.7267 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7262 |
| Basic phospholipase A2 homolog piratoxin-1 | P58399 | PA2H1_BOTPI | Bothrops pirajai | 4 | 0.7259 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7243 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7217 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7201 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7186 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7186 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7179 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7173 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7166 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7152 |
| Uncharacterized protein MJ0489 | Q57913 | Y489_METJA | Methanocaldococcus jannaschii | 4 | 0.7136 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7134 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7129 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7109 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7090 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7078 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7064 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 5 | 0.7044 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7040 |
| Uridine phosphorylase | Q9KT71 | Q9KT71_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7029 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7012 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7005 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7001 |