Penta-O-galloyl-glucose - Compound Card

Penta-O-galloyl-glucose

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Penta-O-galloyl-glucose

Structure
Zoomed Structure
  • 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]
Pubchem: 65238
Kegg Ligand: C04576
Chebi: 18082
Nmrshiftdb2: 60025687
Metabolights: MTBLC18082
Bindingdb: 50241052
CPRiL: 7589
Structure

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

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CC(OC(=O)c4ccccc4)C(O2)OC(=O)c5ccccc5

Level: 4

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)CC(O2)OC(=O)c5ccccc5

Level: 4

Mol. Weight: 940.68 g/mol

Structure

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

Level: 4

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2OC(COC(=O)c3ccccc3)CC(OC(=O)c4ccccc4)C2OC(=O)c5ccccc5

Level: 4

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)OCC2OC(=O)c5ccccc5

Level: 4

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCC(OC(=O)c3ccccc3)C(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)CC(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

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

Level: 3

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CCC(O2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

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

Level: 3

Mol. Weight: 940.68 g/mol

Structure

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

Level: 3

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)OCC(C2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

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

Level: 3

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)COC(C2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)CCOC2OC(=O)c4ccccc4

Level: 3

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCC(OC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CC(OCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(OCCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 940.68 g/mol

Structure

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

Level: 2

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 940.68 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 940.68 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 940.68 g/mol

Antioxidant
Antiviral
Cytotoxic

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

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