3'-O-methyl-4-O-(beta-D-xylopyranosyl) ellagic acid - Compound Card

3'-O-methyl-4-O-(beta-D-xylopyranosyl) ellagic acid

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3'-O-methyl-4-O-(beta-D-xylopyranosyl) ellagic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Glycoside
Canonical Smiles COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O[C@H]1OC[C@@H]([C@H]([C@H]1O)O)O)O
InChI InChI=1S/C20H16O12/c1-28-15-7(21)2-5-11-10-6(19(27)32-17(11)15)3-9(13(24)16(10)31-18(5)26)30-20-14(25)12(23)8(22)4-29-20/h2-3,8,12,14,20-25H,4H2,1H3/t8-,12+,14+,20+/m0/s1
InChIKey VAXNJGHUQUHOGC-RNXJEDPASA-N
Formula C20H16O12
HBA 12
HBD 5
MW 448.34
Rotatable Bonds 3
TPSA 189.26
LogP -0.27
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 448.06
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992

Showing of synonyms

  • 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]
Pubchem: 162933234
Nmrshiftdb2: 80004700

No compound-protein relationship available.

Structure

SMILES: c12c3c4c(=O)oc2cc(OC5CCCCO5)cc1c(=O)oc3ccc4

Level: 1

Mol. Weight: 448.34 g/mol

Structure

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

Level: 0

Mol. Weight: 448.34 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.34 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.36
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.110
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.380
Plasma Protein Binding
79.01
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
9.670
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.830
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
-94.780
Rat (Acute)
2.440
Rat (Chronic Oral)
3.610
Fathead Minnow
4.540
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
585.550
Hydration Free Energy
-3.720
Log(D) at pH=7.4
1.830
Log(P)
-0.47
Log S
-4.18
Log(Vapor Pressure)
-10.57
Melting Point
209.37
pKa Acid
6.78
pKa Basic
2.62
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 0.9450
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9450
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9232
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9232
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9009
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9009
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8950
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8950
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8871
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8871
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8733
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8733
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8727
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8727
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8689
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8689
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8634
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8634
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8626
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8626
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8603
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8603
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8554
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8554
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8475
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8475
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8376
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8376
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8347
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8347
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8294
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8294
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8284
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8284
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8250
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8250
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8120
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8120
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8106
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8106
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8016
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8016
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7924
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7924
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7846
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7846
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7841
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7841
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7812
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7812
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7804
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7804
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7804
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7804
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7801
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7801
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7800
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7800
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7773
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7773
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7745
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7745
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7716
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7716
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7689
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7689
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7682
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7682
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7659
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7659
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7616
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7616
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7613
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7613
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 5 0.7521
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 5 0.7521
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7498
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7498
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7484
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7484
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7454
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7454
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7440
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7440
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7413
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7413
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7396
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7396
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7381
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7381
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7366
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7366
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7363
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7363
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7358
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7358
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7347
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7347
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7338
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7338
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7309
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7309
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7306
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7306
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7300
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7300
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7281
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7281
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7278
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7278
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7259
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7259
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7251
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7251
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7247
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7247
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7241
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7240
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7240
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7240
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7240
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7236
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7236
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7140
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7140
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7130
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7130
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7126
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7126
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7125
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7125
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7084
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7084
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7043
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7043
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7022
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7013
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7013
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
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7004
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7004

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