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

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

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

Structure
Zoomed Structure
  • Family: Irvingiaceae, Dipterocarpaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Derivative
Canonical Smiles COc1c(OC2OCC(C(C2O)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
InChIKey UDWUZPSSUIWBKB-UHFFFAOYSA-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 Monotes kerstingii Dipterocarpaceae Plantae 2029430
2 Desbordesia glaucescens Irvingiaceae Plantae 300981

Showing of synonyms

  • Fotso GW, Mogue Kamdem L, et al. (2019). Antimicrobial secondary metabolites from the stem barks and leaves of Monotes kerstingii Gilg (Dipterocarpaceae).. Fitoterapia,2019, 137, 104239. [View] [PubMed]
  • Kuete V, Dongmo Mafodong F, et al. (2017). In vitro cytotoxicity of compounds isolated from Desbordesia glaucescens against human carcinoma cell lines. South African Journal of Botany, 2017, 111, 37-43. [View]
Pubchem: 14463056
Nmrshiftdb2: 70048157

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 338.31 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

Antibacterial

Absorption

Caco-2 (logPapp)
-6.16
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.440
Plasma Protein Binding
55.64
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
6.330
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.000
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
6.240
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
-156.600
Rat (Acute)
2.420
Rat (Chronic Oral)
3.540
Fathead Minnow
4.900
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
566.090
Hydration Free Energy
-3.320
Log(D) at pH=7.4
2.460
Log(P)
-0.32
Log S
-4.08
Log(Vapor Pressure)
-10.07
Melting Point
206.78
pKa Acid
6.75
pKa Basic
1.75
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 0.9462
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9245
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8952
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8940
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8888
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8740
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8721
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8651
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8626
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8529
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8494
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8470
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8375
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8374
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8311
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8227
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8197
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8179
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8141
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8132
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8108
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8056
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8051
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7991
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7916
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7913
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7872
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7848
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7808
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7681
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7666
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7657
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7607
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7602
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7598
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7579
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7575
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7556
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7546
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7530
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7522
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7490
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 4 0.7480
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7455
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7450
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7446
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7430
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7418
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7413
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7409
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7405
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7397
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7344
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7331
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7324
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7313
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7291
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7284
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7277
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7266
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7241
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7238
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7237
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7230
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7217
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7210
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7183
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7182
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7168
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7156
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7154
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7128
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7124
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7123
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7080
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7073
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7068
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7048
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7037
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7030
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7023
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7020

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