1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-beta-D-glucose - Compound Card

1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-beta-D-glucose

Select a section from the left sidebar

1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-beta-D-glucose

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Tannin
    • Subclass: Ellagitannin
Canonical Smiles OC1[C@@H](OC2[C@H]([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1c1c(C(=O)OC2)cc(c(c1O)O)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2/t18?,27?,28-,29-,34+/m1/s1
InChIKey NLDMNSXOCDLTTB-UWEYZKTMSA-N
Formula C34H26O22
HBA 22
HBD 13
MW 786.56
Rotatable Bonds 4
TPSA 377.42
LogP 0.69
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 56
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 786.09
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix aphylla Tamaricaceae Plantae 189786
2 Tamarix nilotica Tamaricaceae Plantae 189799

Showing of synonyms

  • Orabi MA, Yoshimura M, et al. (2015). Ellagitannins, gallotannins, and gallo-ellagitannins from the galls of Tamarix aphylla. Fitoterapia,2015,104,55-63. [View] [PubMed]
  • Orabi MA, Taniguchi S, et al. (2009). Monomeric and dimeric hydrolysable tannins of Tamarix nilotica. Phytochemistry,2009,70(10),1286-1293. [View] [PubMed]
Pubchem: 163086348
Nmrshiftdb2: 70060294

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(O2)CC(OC(=O)c3ccccc3)C(OC(=O)c4cccc5)C2COC(=O)c(c6c45)cccc6

Level: 2

Mol. Weight: 786.56 g/mol

Structure

SMILES: c1ccccc1C(=O)OC(O2)CCC(OC(=O)c3cccc4)C2COC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 786.56 g/mol

Structure

SMILES: c1ccccc1C(=O)OC(CCO2)C(OC(=O)c3cccc4)C2COC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 786.56 g/mol

Structure

SMILES: c1cccc(c1c23)C(=O)OCC4C(CCCO4)OC(=O)c2cccc3

Level: 0

Mol. Weight: 786.56 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 786.56 g/mol

Tumor-specific cytotoxic

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
16.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
3082.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.41
Plasma Protein Binding
16.73
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.27
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-70.67
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.27
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
-5588706.71
Rat (Acute)
2.51
Rat (Chronic Oral)
4.28
Fathead Minnow
7064.74
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
618036.93
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-1.97
Log(P)
0.59
Log S
-6.09
Log(Vapor Pressure)
-20410.03
Melting Point
338.78
pKa Acid
-124.75
pKa Basic
6.16
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 0.9278
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9278
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9107
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9107
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8959
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8959
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8754
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8754
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8661
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8661
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8556
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8556
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8540
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8540
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8518
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8518
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8517
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8517
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8484
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8484
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8422
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8422
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8422
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8422
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8312
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8312
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8249
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8249
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8190
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8190
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8160
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8126
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8126
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8124
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8124
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8124
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8124
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8086
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8086
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7802
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7802
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7755
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7755
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7711
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7711
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7660
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7660
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7636
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7636
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7615
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7615
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7598
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7598
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7581
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7581
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7543
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7543
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7523
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7523
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7460
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7460
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7434
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7434
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7421
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7421
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7419
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7419
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7406
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7406
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7375
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7375
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7348
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7348
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7328
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7328
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7298
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7298
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7259
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7259
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7230
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7230
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7221
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7221
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7210
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7210
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7182
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7182
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7172
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7172
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7163
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7163
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7145
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7145
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7139
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7139
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7130
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7130
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7122
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7122
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7119
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7119
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7115
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7115
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7072
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7072
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7038
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7038
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7036
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7036

Download SDF