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

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

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3,3'-di-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[C@H]2OC[C@@H]([C@H]([C@H]2O)O)O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O)OC
InChI InChI=1S/C21H18O12/c1-28-15-8(22)3-6-11-12-7(20(27)32-17(11)15)4-10(16(29-2)18(12)33-19(6)26)31-21-14(25)13(24)9(23)5-30-21/h3-4,9,13-14,21-25H,5H2,1-2H3/t9-,13+,14+,21+/m0/s1
InChIKey UDWUZPSSUIWBKB-MCJSFTGGSA-N
Formula C21H18O12
HBA 12
HBD 4
MW 462.36
Rotatable Bonds 4
TPSA 178.26
LogP 0.03
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 462.08
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: 163032231
Nmrshiftdb2: 80004708

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 462.36 g/mol

Structure

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

Level: 0

Mol. Weight: 462.36 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.36 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.440
Plasma Protein Binding
76.65
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
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
6.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.990
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.200
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
-159.520
Rat (Acute)
2.430
Rat (Chronic Oral)
3.540
Fathead Minnow
4.530
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
571.090
Hydration Free Energy
-3.330
Log(D) at pH=7.4
2.590
Log(P)
-0.44
Log S
-4.15
Log(Vapor Pressure)
-10.64
Melting Point
206.57
pKa Acid
6.73
pKa Basic
1.81
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 0.9484
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9484
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9247
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9247
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8950
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8950
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8879
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8879
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8731
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8731
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8725
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8725
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8647
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8647
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8624
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8624
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8591
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8591
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8540
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8540
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8517
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8517
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
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8446
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8446
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8380
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8380
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8367
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8367
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8332
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8332
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8314
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8314
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8297
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8297
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8196
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8196
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8183
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8183
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8135
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8135
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8128
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8128
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8122
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8122
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7987
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7987
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7967
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7967
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7965
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7965
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7858
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7858
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7849
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7849
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7827
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7827
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7823
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7823
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7783
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7783
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7680
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7680
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7668
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7668
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7593
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7593
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 5 0.7566
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 5 0.7566
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7539
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7539
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7518
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7518
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7491
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7463
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7463
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7447
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7441
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7441
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7440
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7440
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7420
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7420
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7412
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7412
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7406
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7406
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7398
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7398
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7364
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7364
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 0.7359
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7359
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7350
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7350
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7339
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7339
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7311
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7311
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7307
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7307
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7290
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7290
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7278
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7278
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7277
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7277
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7265
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7265
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7263
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7263
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7255
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7255
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7255
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7255
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7254
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7254
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7245
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7245
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7231
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7231
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7229
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7229
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7223
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7223
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7212
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7212
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7180
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7180
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7118
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7111
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7111
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7098
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7098
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7083
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7083
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7075
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7075
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7068
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7068
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7055
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7055
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7037
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7037
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7034
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7034
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7002
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7002

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