Ellagic acid - Compound Card

Ellagic acid

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Ellagic acid

Structure
Zoomed Structure
  • Family: Plantae - Fagaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Polyphenol
Canonical Smiles Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O
InChI InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H
InChIKey AFSDNFLWKVMVRB-UHFFFAOYSA-N
Formula C14H6O8
HBA 8
HBD 4
MW 302.19
Rotatable Bonds 0
TPSA 141.34
LogP 1.31
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 302.01
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992
2 Terminalia arjuna Combretaceae Plantae 172200
3 Euphorbia species Euphorbiaceae Plantae 1501592
4 Lagerstroemia indica Lythraceae Plantae 141186
5 Melaleuca quinquenervia Myrtaceae Plantae 164942
6 Epilobium hirsutum Onagraceae Plantae 210355
7 Sanguisorba minor Rosaceae Plantae 137456
8 Reaumuria vermiculata Tamaricaceae Plantae 1518163
9 Alchornea laxiflora Euphorbiaceae Plantae 316698
10 Quercus ilex Fagaceae Plantae 58334
11 Quercus ilex Fagaceae Plantae 58334

Showing of synonyms

  • Kandil FE, Nassar MI (1998). A tannin anti-cancer promotor from Terminalia arjuna. Phytochemistry,1998,47(8),1567-1568. [View] [PubMed]
  • Saleh NAM (1973). Anthocyanins of Lagerstroemia indica flowers. Phytochemistry,1973,12(9),2304. [View]
  • Siwe-Noundou X, Ndinteh D, et al. (2019). Biological activity of plant extracts and isolated compounds from Alchornea laxiflora: Anti-HIV, antibacterial and cytotoxicity evaluation. South African Journal of Botany, 2019, 122, 498-503. [View]
  • Nawwar MA, Ayoub NA, et al. (2012). Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia,2012,83(7),1256-1266. [View] [PubMed]
  • 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]
  • Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]
  • Moharram FA, Marzouk MS, et al. (2003). Polyphenols of Melaleuca quinquenervia leaves - pharmacological studies of grandinin. Phytotherapy Research,2003,17(7),767-773. [View] [PubMed]
  • Castejón M.L, Rosillo M.Á, et al. (2019). Quercus ilex extract ameliorates acute TNBS-induced colitis in rats. Planta medica, 2019, 85(8), 670-677. [View] [PubMed]
  • Hadidi L, Babou L, et al. (2017). Quercus ilex L.: How season, plant organ and extraction procedure can influence chemistry and bioactivities. Chemistry & Biodiversity, 2017, 14(1),. [View] [PubMed]
  • Kawashty SA, Abdalla MF, et al. (1990). The chemosystematics of Egyptian Euphorbia species. Biochemical Systematics and Ecology,1990,18(7-8),487-490. [View]
  • Ayoub NA (2003). Unique phenolic carboxylic acids from Sanguisorba minor. Phytochemistry,2003,63(4),433-436. [View] [PubMed]
Pubchem: 5281855
Kegg Ligand: C10788
Chebi: 4775
Nmrshiftdb2: 60021292
Metabolights: MTBLC4775
Chembl: CHEMBL6246
Drugbank: DB08846
Pdb Ligand: REF
Bindingdb: 4078
CPRiL: 9671
Structure

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

Level: 0

Mol. Weight: 302.19 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.170
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.310
Plasma Protein Binding
87.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
7.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.740
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.660
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.990
Rat (Acute)
2.310
Rat (Chronic Oral)
3.400
Fathead Minnow
4.220
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
522.220
Hydration Free Energy
-12.580
Log(D) at pH=7.4
1.820
Log(P)
1.02
Log S
-3.74
Log(Vapor Pressure)
-8.54
Melting Point
352.69
pKa Acid
7.74
pKa Basic
4.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9252
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9252
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9049
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9049
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8924
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8924
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8875
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8875
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8873
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8873
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8709
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8709
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8681
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8681
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8680
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8680
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8626
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8626
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8580
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8580
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8498
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8498
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8483
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8483
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8454
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8454
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8229
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8229
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 5 0.8207
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 5 0.8207
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8027
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8027
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7994
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7994
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7938
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7938
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7916
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7916
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7912
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7912
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7909
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7909
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7842
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7842
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7780
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7780
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7753
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7753
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7691
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7691
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7685
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7685
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7678
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7678
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7651
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7651
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7620
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7620
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7553
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7553
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7519
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7519
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7473
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7473
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7424
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7424
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7399
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7399
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7388
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7388
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7388
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7388
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7380
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7380
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7366
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7366
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7319
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7319
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7243
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7243
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7197
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7197
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7183
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7183
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7180
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7180
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7179
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7179
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7167
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7167
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7166
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7166
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7155
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7155
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7144
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7144
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7135
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7135
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7112
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7112
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7102
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7089
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7089
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7087
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7087
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7082
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7082
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7078
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7078
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7055
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7055
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7027
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7027
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7022
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7022
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7015
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7015
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7005

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