3,3''-dimethoxy ellagic acid 4-O-glucoside - Compound Card

3,3''-dimethoxy ellagic acid 4-O-glucoside

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3,3''-dimethoxy ellagic acid 4-O-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OCC1O[C@H](Oc2c(OC)cc3c4c2oc(=O)c2c4c(oc3=O)c(c(c2)OC)O)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C22H20O13/c1-30-8-3-6-11-12-7(20(28)33-18(11)14(8)25)4-9(31-2)17(19(12)34-21(6)29)35-22-16(27)15(26)13(24)10(5-23)32-22/h3-4,10,13,15-16,22-27H,5H2,1-2H3/t10?,13-,15?,16+,22-/m1/s1
InChIKey YQIVRYWOBFTREV-YIUDYMISSA-N
Formula C22H20O13
HBA 13
HBD 5
MW 492.39
Rotatable Bonds 5
TPSA 198.49
LogP -0.61
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 492.09
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Harpephyllum caffrum Anacardiaceae Plantae 289712

Showing of synonyms

  • Nawwar M, Hussein S, et al. (2011). Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia,2011,82(8),1265-1271. [View] [PubMed]
Pubchem: 162997901
Nmrshiftdb2: 60028418

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(c2oc(=O)c3c4c25)ccc5c(=O)oc4ccc3

Level: 1

Mol. Weight: 492.39 g/mol

Structure

SMILES: c12c3c4c(=O)oc2cccc1c(=O)oc3ccc4

Level: 0

Mol. Weight: 492.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.23
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.97
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.28
Plasma Protein Binding
71.83
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
7.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.75
Micronucleos
Toxic
NR-AhR
Safe
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
-412.72
Rat (Acute)
2.4
Rat (Chronic Oral)
3.83
Fathead Minnow
4.95
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
595.09
Hydration Free Energy
-3.17
Log(D) at pH=7.4
1.85
Log(P)
-0.96
Log S
-4.01
Log(Vapor Pressure)
-10.46
Melting Point
194.4
pKa Acid
5.59
pKa Basic
2.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9371
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9371
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9105
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9105
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9030
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9030
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8976
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8976
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8972
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8972
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8780
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8780
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8673
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8673
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8651
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8651
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8584
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8584
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8547
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8547
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8439
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8439
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8398
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8398
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8295
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8295
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8257
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8257
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8225
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8225
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8172
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8172
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8095
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8095
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8089
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8089
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8002
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8002
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7951
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7951
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7937
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7937
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.7876
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.7876
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7833
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7833
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7820
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7820
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7788
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7788
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7772
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7772
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7622
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7622
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7612
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7612
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7480
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7480
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 4 0.7473
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 4 0.7473
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7471
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7471
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7459
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7459
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7409
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7409
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7396
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7390
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7390
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7372
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7372
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7341
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7341
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7329
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7329
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7326
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7326
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7323
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7323
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7318
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7318
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7307
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7307
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7299
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7299
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7297
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7297
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7274
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7274
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7267
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7267
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7264
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7264
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7259
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7259
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7244
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7244
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7233
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7233
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7226
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7226
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7226
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7226
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7218
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7218
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7209
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7209
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7203
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7203
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7198
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7198
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7184
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7184
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7137
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7137
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7129
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7129
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7116
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7116
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7113
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7113
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7110
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7110
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7098
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7098
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7067
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7067
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7056
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7056
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7048
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7048
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7044
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7044
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7033
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7033
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7033
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7033
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 4 0.7028
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 4 0.7028
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7021
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7021

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