Canthoside B - Compound Card

Canthoside B

Select a section from the left sidebar

Canthoside B

Structure
Zoomed Structure
  • Family: Plantae - Juncaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles COc1cc(O[C@@H]2O[C@H](CO[C@@H]3OC[C@]([C@H]3O)(O)CO)[C@H]([C@@H]([C@H]2O)O)O)cc(c1O)OC
InChI InChI=1S/C19H28O13/c1-27-9-3-8(4-10(28-2)12(9)21)31-17-15(24)14(23)13(22)11(32-17)5-29-18-16(25)19(26,6-20)7-30-18/h3-4,11,13-18,20-26H,5-7H2,1-2H3/t11-,13-,14+,15-,16+,17-,18-,19-/m1/s1
InChIKey BPSJMBKZSUTYNF-CYKPCRQUSA-N
Formula C19H28O13
HBA 13
HBD 7
MW 464.42
Rotatable Bonds 8
TPSA 196.99
LogP -2.95
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 464.15
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Juncus acutus Juncaceae Plantae 308385

Showing of synonyms

  • Awaad AS (2006). Phenolic glycosides of Juncus acutus and its anti-eczematic activity. Chemistry of Natural Compounds,2006,42(2),152-155. [View]
Pubchem: 102022260
Nmrshiftdb2: 70071681

No compound-protein relationship available.

Structure

SMILES: O1CCCC1OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 464.42 g/mol

Structure

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 464.42 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 464.42 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 464.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 464.42 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 464.42 g/mol

Anti-eczematic

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.400
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
63.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.260
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.980
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.150
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
-65.910
Rat (Acute)
1.910
Rat (Chronic Oral)
3.820
Fathead Minnow
3.320
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
522.440
Hydration Free Energy
-5.240
Log(D) at pH=7.4
-1.110
Log(P)
-2.23
Log S
-2.4
Log(Vapor Pressure)
-14.44
Melting Point
182.71
pKa Acid
4.75
pKa Basic
4.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9059
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9059
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8976
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8976
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8722
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8722
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8674
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8674
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8594
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8594
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8536
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8536
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8463
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8463
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8390
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8390
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8272
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8272
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8239
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8239
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8218
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8218
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8142
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8142
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7924
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7924
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7904
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7904
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7902
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7902
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7874
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7874
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7692
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7692
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7667
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7667
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7666
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7666
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7621
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7621
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7616
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7616
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7576
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7576
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7530
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7530
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7487
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7487
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7487
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7487
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7412
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7412
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7402
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7402
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7400
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7400
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7312
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7312
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7304
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7304
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7299
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7277
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7277
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7276
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7276
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7267
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7267
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7248
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7248
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 4 0.7238
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 4 0.7238
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7182
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7182
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7178
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7178
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7136
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7136
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7081
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7081
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7078
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7078
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7076
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7076
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7074
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7074
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7072
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7072
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7070
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7070
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7067
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7067
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7056
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7056
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7032
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7032
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7029
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7029
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7015
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7015
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7009
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7009
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7005
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7005
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7004
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7004

Download SDF