3,3′′-di-O-methylellagic acid 4-O-(3′′-galloyl)-beta-D-xylopyranoside - Compound Card

3,3′′-di-O-methylellagic acid 4-O-(3′′-galloyl)-beta-D-xylopyranoside

Select a section from the left sidebar

3,3′′-di-O-methylellagic acid 4-O-(3′′-galloyl)-beta-D-xylopyranoside

Structure
Zoomed Structure
  • Family: Burseraceae
  • Kingdom: Plantae
  • Class: Tannin
    • Subclass: Ellagitannin
Canonical Smiles COc1c(OC2OCC(C(C2O)OC(=O)c2cc(O)c(c(c2)O)O)O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O)OC
InChI InChI=1S/C28H22O16/c1-38-21-13(31)5-9-16-17-10(27(37)43-23(16)21)6-15(22(39-2)24(17)44-26(9)36)41-28-19(34)20(14(32)7-40-28)42-25(35)8-3-11(29)18(33)12(30)4-8/h3-6,14,19-20,28-34H,7H2,1-2H3
InChIKey NSQYRRYPZPIMLH-UHFFFAOYSA-N
Formula C28H22O16
HBA 16
HBD 6
MW 614.47
Rotatable Bonds 6
TPSA 245.02
LogP 1.01
Number Rings 6
Number Aromatic Rings 5
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 614.09
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Dacryodes edulis Burseraceae Plantae 246365

Showing of synonyms

  • Dongmo KJJ, Tali MBT, et al. (2023). In vitro antiplasmodial activity and toxicological profile of extracts, fractions and chemical constituents of leaves and stem bark from Dacryodes edulis (Burseraceae).. BMC complementary medicine and therapies,2023, 23(1), 211. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CC(OCC2)Oc(cc3oc(=O)c4c5c36)cc6c(=O)oc5ccc4

Level: 2

Mol. Weight: 458.42 g/mol

Structure

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

Level: 1

Mol. Weight: 338.31 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 206.24 g/mol

Structure

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

Level: 0

Mol. Weight: 238.2 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-6.32
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.070
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
16.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.400
Plasma Protein Binding
52.18
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
10.950
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.990
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.680
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
-31325.520
Rat (Acute)
2.510
Rat (Chronic Oral)
3.970
Fathead Minnow
60.460
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
409.930
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.320
Log(P)
0.45
Log S
-5.46
Log(Vapor Pressure)
-18.86
Melting Point
231.31
pKa Acid
7.18
pKa Basic
0.21
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 0.9503
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9351
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9335
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9232
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9034
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8996
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8962
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8945
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8941
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8766
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8687
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8640
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8631
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8578
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8515
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8508
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8461
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8452
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8426
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8417
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8390
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8359
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8333
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8282
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8268
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8257
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8224
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8207
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8175
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8159
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8152
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8091
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8059
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8055
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8022
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8017
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7995
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7993
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7974
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7943
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7898
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7897
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7890
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7849
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7800
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7788
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7780
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7761
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7740
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7728
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.7723
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7708
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7699
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7696
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7683
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7677
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7648
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7646
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7632
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7624
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7602
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7582
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7556
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7555
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7495
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7488
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7486
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 4 0.7479
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7456
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7442
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7439
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7433
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7422
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7421
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7421
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7404
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7380
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7362
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7352
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7326
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7317
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7299
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7293
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7292
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7286
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7285
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7279
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7272
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7270
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7267
Mitogen-activated protein kinase FUS3 P16892 FUS3_YEAST Saccharomyces cerevisiae 4 0.7262
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7262
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7241
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7240
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7233
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7221
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7219
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7178
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7171
Glucanase B7X9Z2 B7X9Z2_COPCI Coprinopsis cinerea 4 0.7170
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7169
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7158
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7155
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7154
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7148
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7141
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7132
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7084
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7061
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7051
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7042
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7019

Download SDF