Syringaresinol-4-O-beta-D-glucopyranoside - Compound Card

Syringaresinol-4-O-beta-D-glucopyranoside

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Syringaresinol-4-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles COc1cc(cc(c1O)OC)C1OCC2C1COC2c1cc(OC)c(c(c1)OC)O
InChI InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3
InChIKey KOWMJRJXZMEZLD-UHFFFAOYSA-N
Formula C22H26O8
HBA 8
HBD 2
MW 418.44
Rotatable Bonds 6
TPSA 95.84
LogP 3.21
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 418.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea microphylla Thymelaeaceae Plantae 224056

Showing of synonyms

  • Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]
Pubchem: 100067
Chebi: 49211
Nmrshiftdb2: 60021821
Metabolights: MTBLC49211
CPRiL: 91565
Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 418.44 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 418.44 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 418.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 418.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.960
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.930
Plasma Protein Binding
18.88
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
11.460
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.620
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.780
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.660
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-46.760
Rat (Acute)
2.100
Rat (Chronic Oral)
2.340
Fathead Minnow
4.970
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
445.190
Hydration Free Energy
-3.680
Log(D) at pH=7.4
2.670
Log(P)
1.35
Log S
-4.0
Log(Vapor Pressure)
-8.13
Melting Point
171.56
pKa Acid
8.39
pKa Basic
2.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9286
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.9155
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8948
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8812
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8799
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8694
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8676
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8640
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8629
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8571
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.8431
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8361
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8317
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8206
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8191
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8134
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8133
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8043
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8040
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8017
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8006
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7945
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 4 0.7877
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 4 0.7870
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 4 0.7843
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7829
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7828
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7778
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7749
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7734
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7723
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7661
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7607
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7605
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7581
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7488
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7471
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7464
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7441
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7396
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7385
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7381
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7381
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7351
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7343
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7303
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7294
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7263
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7249
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7239
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7239
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7233
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7219
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7206
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7205
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7195
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7186
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7141
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7133
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7130
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7122
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7115
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7110
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.7093
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7088
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7083
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7082
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7074
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7069
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7066
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7046
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7019

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