Select a section from the left sidebar
Syringaresinol-4-O-beta-D-glucopyranoside
- 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
Syringaresinol-4-O-beta-D-glucopyranoside
Syringaresinol
1177-14-6
487-35-4
DL-Syringaresinol
4-[6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
4,4'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2,6-dimethoxyphenol)
Phenol,4,4'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2,6-dimethoxy-
(+/-)-Syringaresinol
21453-71-4
(+)-Episyringaresinol
551-29-1
Symplicosigenol
Syringylresinol
Lirioresinol A
Bmse010057
4,4'-tetrahydro-1h,3h-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)
SCHEMBL120485
CHEMBL4469429
CHEBI:49211
BCA15220
BCP19980
BCP19981
HY-N8307
MSK165457
(-)-Lirioresinol B
AKOS032948292
S(8-8)S
DA-52609
DA-78139
FS-10194
Phenol,4,4'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2,6-dimethoxy-,(1R,3aS,4R,6aS)-rel-
DS-012209
CS-0142910
A893311
Q27121534
3,3,5,5-tetramethoxy-7,9,7,9-diepoxylignan-4,4-diol
3,3',5,5'-tetramethoxy-7,9':7',9-diepoxylignane-4,4'-diol
4-[6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol
Phenol,4,4-[(1s,3ar,4s,6ar)-tetrahydro-1h,3h-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy-
Syringaresinol487-35-4
Pubchem:
100067
Cas:
1177-14-6
Gnps:
CCMSLIB00005720300
Chebi:
49211
Nmrshiftdb2:
60021821
Metabolights:
MTBLC49211
Chembl:
CHEMBL4469429
CPRiL:
91565
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4
Level: 2
Mol. Weight: 418.44 g/mol
SMILES: C1OCC(C12)COC2c3ccccc3
Level: 1
Mol. Weight: 418.44 g/mol
SMILES: C1OCC(C12)COC2
Level: 0
Mol. Weight: 418.44 g/mol
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 |