Penta-O-galloyl-glucose
- Family: Plantae - Anacardiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Gallic Acid Derivative
Canonical Smiles | O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)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)OC(=O)c1cc(O)c(c(c1)O)O |
---|---|
InChI | InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1 |
InChIKey | QJYNZEYHSMRWBK-NIKIMHBISA-N |
Formula | C41H32O26 |
HBA | 26 |
HBD | 15 |
MW | 940.68 |
Rotatable Bonds | 11 |
TPSA | 444.18 |
LogP | 1.69 |
Number Rings | 6 |
Number Aromatic Rings | 5 |
Heavy Atom Count | 67 |
Formal Charge | 0 |
Fraction CSP3 | 0.15 |
Exact Mass | 940.12 |
Number of Lipinski Rule Violations | 3 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Mangifera indica | Anacardiaceae | Plantae | 29780 |
2 | Cornulaca monacantha | Chenopodiaceae | Plantae | 454476 |
3 | Terminalia species | Combretaceae | Plantae | 39992 |
4 | Nymphaea lotus | Nymphaeaceae | Plantae | 264924 |
5 | Harpullia pendula | Sapindaceae | Plantae | 884417 |
6 | Anacardium occidentale | Anacardiaceae | Plantae | 171929 |
Showing of synonyms
- Abdel-Mageed WM, Bayoumi SAH, et al. (2014). Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorganic and Medicinal Chemistry,2014,22(7),2236-2243. [View] [PubMed]
- Ghaly N, Nabil M, et al. (2017). Pendulaosides A and B. Two acylated triterpenoid saponins from Harpullia pendula seed extract. Phytochemistry Letters, 2017, 21, 278-282. [View]
- Taiwo Bamigboye J, Popoola Temidayo D, et al. (2020). Pentagalloylglucose, isolated from the leaf extract of Anacardium occidentale L., could elicit rapid and selective cytotoxicity in cancer cells. BMC Complementary Medicine and Therapies, 2020, 20(1),287 (2020). [View]
- 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]
- Kandil FE, Grace MH (2001). Polyphenols from Cornulaca monacantha. Phytochemistry,2001,58(4),611-613. [View] [PubMed]
- Elegami AA, Bates C, et al. (2003). Two very unusual macrocyclic flavonoids from the water lily Nymphaea lotus. Phytochemistry,2003,63(6),727-731. [View] [PubMed]
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)C(OC(=O)c5ccccc5)C(O2)OC(=O)c6ccccc6
Level: 5
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CC(OC(=O)c4ccccc4)C(O2)OC(=O)c5ccccc5
Level: 4
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)CC(O2)OC(=O)c5ccccc5
Level: 4
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)C(CO2)OC(=O)c5ccccc5
Level: 4
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2OC(COC(=O)c3ccccc3)CC(OC(=O)c4ccccc4)C2OC(=O)c5ccccc5
Level: 4
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)OCC2OC(=O)c5ccccc5
Level: 4
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CCC(OC(=O)c3ccccc3)C(O2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)CC(O2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)C(CO2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CCC(O2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CC(CO2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(CCO2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)OCC(C2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)COCC2OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)COC(C2)OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)CCOC2OC(=O)c4ccccc4
Level: 3
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CCC(CO2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CC(CCO2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2C(CCCO2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CCC(OC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CC(OCC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CC(COC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(OCCC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3ccccc3
Level: 2
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OCC2CCCCO2
Level: 1
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CCOCC2
Level: 1
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CCCOC2
Level: 1
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1C(=O)OC2CCCCO2
Level: 1
Mol. Weight: 940.68 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 940.68 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 940.68 g/mol
Absorption
- Caco-2 (logPapp)
- -6.54
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 3533.95
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 462706.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.34
- Plasma Protein Binding
- 15.99
- 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
- Inhibitor
Excretion
- Clearance
- 12.28
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -10750.99
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.11
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.05
- 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
- -839787443.57
- Rat (Acute)
- 2.55
- Rat (Chronic Oral)
- 5.63
- Fathead Minnow
- 1060063.34
- 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
- 94440642.65
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -40.6
- Log(P)
- 1.13
- Log S
- -7.62
- Log(Vapor Pressure)
- -3109925.73
- Melting Point
- 388.79
- pKa Acid
- -22616.06
- pKa Basic
- -149.08
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 | 0.9230 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9230 |
rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9079 |
rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9079 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8633 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8633 |
Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8513 |
Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8513 |
WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8409 |
WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8409 |
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8263 |
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8263 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8246 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8246 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8137 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8137 |
Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8136 |
Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8136 |
Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7873 |
Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7873 |
Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7646 |
Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7646 |
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7572 |
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7572 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7520 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7520 |
NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7490 |
NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7490 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7437 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7437 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7376 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7376 |
Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7281 |
Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7281 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7264 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7264 |
Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 4 | 0.7195 |
Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 4 | 0.7195 |
Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7194 |
Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7194 |
Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7159 |
Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7159 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7145 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7145 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7112 |
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7112 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7104 |
HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7104 |
Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7069 |
Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7069 |