(+)-lyoniresinol-3a-O-beta-D-glucopyranoside - Compound Card

(+)-lyoniresinol-3a-O-beta-D-glucopyranoside

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(+)-lyoniresinol-3a-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Cyclolignan
Canonical Smiles OC[C@@H]1Cc2cc(OC)c(c(c2[C@@H](C1CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1cc(OC)c(c(c1)OC)O)OC)O
InChI InChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(11-40-28-26(35)25(34)23(32)19(10-30)41-28)14(9-29)5-12-6-18(38-3)24(33)27(39-4)21(12)20/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3/t14-,15?,19+,20+,23+,25-,26+,28+/m0/s1
InChIKey PQQRNPDHSJDAGV-HUVRXQFXSA-N
Formula C28H38O13
HBA 13
HBD 7
MW 582.6
Rotatable Bonds 10
TPSA 196.99
LogP -0.14
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 582.23
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Boscia senegalensis Capparaceae Plantae 1198336

Showing of synonyms

  • Morgan AMA, Lim CH, et al. (2015). Lignans, cyclolignans and neolignans from the leaves of Boscia senegalensis (Pers.) Lam. ex Poir.. Biochemical Systematics and Ecology,2015,59,226-228. [View]
Pubchem: 162939855
Nmrshiftdb2: 60049675

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(C2c3ccccc3)CCc(c24)cccc4

Level: 2

Mol. Weight: 582.6 g/mol

Structure

SMILES: O1CCCCC1OCC(C2)CCc(c23)cccc3

Level: 1

Mol. Weight: 582.6 g/mol

Structure

SMILES: c1cccc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 582.6 g/mol

Structure

SMILES: C1CCCc(c12)cccc2

Level: 0

Mol. Weight: 582.6 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 582.6 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 582.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.320
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
64.3
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.600
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.340
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
-5755.010
Rat (Acute)
2.460
Rat (Chronic Oral)
4.210
Fathead Minnow
14.820
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
481.070
Hydration Free Energy
-2.940
Log(D) at pH=7.4
0.210
Log(P)
-1.09
Log S
-4.05
Log(Vapor Pressure)
-10.33
Melting Point
179.55
pKa Acid
5.91
pKa Basic
4.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9618
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9618
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9040
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9040
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8738
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8738
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8586
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8586
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8549
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8549
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8406
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8406
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8214
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8214
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.8174
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.8174
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8144
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8144
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7950
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7950
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7817
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7817
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7769
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7769
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7723
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7723
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7625
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7625
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7568
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7568
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7526
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7526
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7503
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7503
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7411
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7411
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7259
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7259
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7244
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7244
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7211
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7211
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7210
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7210
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7142
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.7142
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7128
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7128
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7114
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7114
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7108
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7108
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7094
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7094
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7093
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7093
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7054
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7054
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7036
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7036
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7026
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7026
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7025
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7025

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