Dehydrodiconiferyl alcohol-4-O-beta-D-glucopyranoside - Compound Card

Dehydrodiconiferyl alcohol-4-O-beta-D-glucopyranoside

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Dehydrodiconiferyl alcohol-4-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Lignan Glycoside
Canonical Smiles OC/C=C/c1cc(OC)c2c(c1)[C@H](CO)[C@H](O2)c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C26H32O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-6,8-10,16,20-24,26-32H,7,11-12H2,1-2H3/b4-3+/t16-,20+,21+,22-,23+,24+,26+/m0/s1
InChIKey SPWHQAUMLDQOFU-QXGRHDLQSA-N
Formula C26H32O11
HBA 11
HBD 6
MW 520.53
Rotatable Bonds 9
TPSA 167.53
LogP 0.1
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 520.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Boscia senegalensis Capparaceae Plantae 1198336
2 Teucrium polium Lamiaceae Plantae 1117157

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]
  • Elmasri W.A, Yang T, et al. (2015). Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus. Journal of natural products, 2015, 78(1), 2-9. [View] [PubMed]
Pubchem: 5316442
Nmrshiftdb2: 60070061

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 520.53 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 520.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 520.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
85.59
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
6.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.86
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
-1217.69
Rat (Acute)
2.59
Rat (Chronic Oral)
3.93
Fathead Minnow
5.39
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
544.19
Hydration Free Energy
-2.98
Log(D) at pH=7.4
1.04
Log(P)
-0.67
Log S
-3.66
Log(Vapor Pressure)
-11.14
Melting Point
196.39
pKa Acid
6.86
pKa Basic
1.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9340
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9340
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8927
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8927
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8882
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8882
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8610
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8610
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8569
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8569
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8533
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8533
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8509
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8509
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8421
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8421
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8237
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8213
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8213
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8044
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8044
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7992
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7992
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7991
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7991
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7920
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7920
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7834
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7834
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7813
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7813
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7755
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7755
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7669
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7669
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7654
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7654
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7653
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7653
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7585
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7585
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7559
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7559
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7528
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7528
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7457
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7457
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7444
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7444
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7416
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7416
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7406
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7406
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7317
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7317
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7284
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7284
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7243
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7243
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7240
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7240
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7217
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7217
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7212
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7212
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7207
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7207
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7199
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7199
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7129
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7129
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7122
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7122
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7112
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7112
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7101
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7101
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7094
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7094
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7066
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7066
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7058
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7058
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7033
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7033
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7015
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7015

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