(-)-lyoniresinol-3alpha-O-beta-D-glucopyranoside - Compound Card

(-)-lyoniresinol-3alpha-O-beta-D-glucopyranoside

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(-)-lyoniresinol-3alpha-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC[C@H]1Cc2cc(OC)c(c(c2[C@H]([C@@H]1CO[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+/m1/s1
InChIKey PQQRNPDHSJDAGV-CIPGMYPZSA-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: 124899947

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)
-6.56
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
70.31
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
-2.160
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
-5754.770
Rat (Acute)
2.460
Rat (Chronic Oral)
4.200
Fathead Minnow
14.800
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
482.250
Hydration Free Energy
-2.940
Log(D) at pH=7.4
0.220
Log(P)
-1.15
Log S
-4.05
Log(Vapor Pressure)
-10.38
Melting Point
175.43
pKa Acid
5.88
pKa Basic
4.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9081
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.9056
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8877
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8872
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8830
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8775
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8715
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8705
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8574
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8518
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8145
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8051
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8007
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7912
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7648
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7623
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7591
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7477
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7405
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7393
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7392
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7333
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7317
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7273
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7219
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7195
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7184
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7172
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7166
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7161
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7126
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7055
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7048
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7032
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7029
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7018
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7018
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7016
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7011

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