Methyl ellagic acid - Compound Card

Methyl ellagic acid

Select a section from the left sidebar

Methyl ellagic acid

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Acid Derivative
Canonical Smiles COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O)O
InChI InChI=1S/C15H8O8/c1-21-11-7(17)3-5-9-8-4(15(20)23-13(9)11)2-6(16)10(18)12(8)22-14(5)19/h2-3,16-18H,1H3
InChIKey FAARLWTXUUQFSN-UHFFFAOYSA-N
Formula C15H8O8
HBA 8
HBD 3
MW 316.22
Rotatable Bonds 1
TPSA 130.34
LogP 1.62
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 316.02
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992
2 Melaleuca quinquenervia Myrtaceae Plantae 164942
3 Reaumuria vermiculata Tamaricaceae Plantae 1518163
4 Terminalia brownii Combretaceae Plantae 1548809
5 Terminalia mantaly Combretaceae Plantae 578553
6 Alchornea laxiflora Euphorbiaceae Plantae 316698

Showing of synonyms

  • 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]
  • Tchuente Tchuenmogne MA, Kammalac TN, et al. (2017). Compounds from Terminalia mantaly L. (Combretaceae) Stem Bark Exhibit Potent Inhibition against Some Pathogenic Yeasts and Enzymes of Metabolic Significance. Medicines (Basel). 2017, 4(1), 6. [View] [PubMed]
  • Nawwar MA, Ayoub NA, et al. (2012). Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia,2012,83(7),1256-1266. [View] [PubMed]
  • Machumi F, Midiwo JO, et al. (2013). Phytochemical, antimicrobial and antiplasmodial investigations of Terminalia brownii. Natural Product Communications,2013,8(6),761-764. [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]
  • 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]
Pubchem: 13915428
Nmrshiftdb2: 60026606

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 316.22 g/mol

Antimicrobial
Antioxidant

Absorption

Caco-2 (logPapp)
-5.32
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
85.55
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
6.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.040
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.460
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
2.850
Rat (Acute)
2.330
Rat (Chronic Oral)
3.040
Fathead Minnow
4.580
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
503.580
Hydration Free Energy
-9.710
Log(D) at pH=7.4
3.100
Log(P)
1.3
Log S
-4.94
Log(Vapor Pressure)
-7.61
Melting Point
301.3
pKa Acid
8.84
pKa Basic
2.22
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 0.9443
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9443
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9233
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9233
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9040
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9040
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8946
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8946
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8881
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8881
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8833
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8833
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8817
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8817
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8811
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8811
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8703
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8703
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8659
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8659
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8583
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8583
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8528
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8528
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8491
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8491
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8328
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8328
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8265
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8265
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8234
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8234
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 5 0.8226
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 5 0.8226
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8141
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8141
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8104
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8104
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8096
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8096
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.8078
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.8078
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8022
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8022
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7962
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7930
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7930
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7913
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7913
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7911
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7911
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7801
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7801
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7785
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7785
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7723
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7723
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7718
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7718
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7681
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7681
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7634
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7634
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7615
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7615
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7568
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7568
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7556
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7556
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7544
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7544
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7508
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7508
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7494
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7494
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7479
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7479
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7453
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7453
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7431
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7431
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7424
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7424
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7394
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7394
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7369
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7369
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7361
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7361
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7361
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7361
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7355
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7355
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7348
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7348
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7281
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7281
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7275
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7275
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7253
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7253
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7238
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7238
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7236
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7236
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7227
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7227
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7222
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7222
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7217
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7217
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7210
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7210
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7199
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7199
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7189
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7189
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7165
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7165
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7103
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7103
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7087
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7087
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7080
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7080
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7071
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7071
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7071
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7071
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7068
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7068
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7038
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7038
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7019
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7019
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7012
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7012

Download SDF