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Syringin
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenylpropanoid Glycoside
| Canonical Smiles | OC/C=C/c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1 |
| InChIKey | QJVXKWHHAMZTBY-GCPOEHJPSA-N |
| Formula | C17H24O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 372.37 |
| Rotatable Bonds | 7 |
| TPSA | 138.07 |
| LogP | -1.11 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 372.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sanchezia nobilis | Acanthaceae | Plantae | 71612 |
| 2 | Ruellia tuberosa | Acanthaceae | Plantae | 441035 |
| 3 | Ruellia patula | Acanthaceae | Plantae | 441006 |
| 4 | Chrozophora obliqua | Euphorbiaceae | Plantae | 316753 |
Showing of synonyms
Syringin
Eleutheroside B
118-34-3
Syringoside
Lilacin
Methoxyconiferine
Ligustrin
Syrigin
Syringenin
MAGNOLENIN A
Sinapyl alcohol 4-O-glucoside
Ilexanthin A
Magnolenin
Magmolenin A
UNII-I6F5B11C96
CHEBI:9380
I6F5B11C96
NSC 287441
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl beta-D-glucopyranoside
DTXSID2042438
NSC-287441
Glucoside, 4-(3-hydroxypropenyl)-2,6-dimethoxyphenyl, D
Sinapyl alcohol-4-O-beta-D-glucopyranoside
ELEUTHEROSIDE B (USP-RS)
ELEUTHEROSIDE B [USP-RS]
Beta-D-Glucopyranoside, 4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenyl
Beta-D-Glucopyranoside, 4-((1E)-3-hydroxy-1-propenyl)-2,6-dimethoxyphenyl
4-((1E)-3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenyl beta-D-glucopyranoside
DTXCID0022438
4-O-(beta-D-glucosyl)-trans-4-sinapoyl alcohol
ELEUTHEROSIDE B (CONSTITUENT OF ELEUTHERO)
4-((1E)-3-HYDROXY-1-PROPEN-1-YL)-2,6-DIMETHOXYPHENYL-beta-D-GLUCOPYRANOSIDE
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
CHEMBL250872
.beta.-Terpineol
Ligustrin (VAN)
Syringinenin
NSC287441
MFCD00016778
Syringin (Standard)
SYRINGIN [MI]
Bmse000613
MLS000574917
SCHEMBL409032
MEGxp0_000264
ACon1_000108
HY-N0824R
QJVXKWHHAMZTBY-GCPOEHJPSA-N
HMS2217D04
HMS3885E08
HY-N0824
MSK40085
Eleutheroside B, analytical standard
BDBM50241356
NSC791584
S3841
AKOS015912605
CCG-268321
MS10479
NSC-791584
NCGC00180873-01
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxy-phenoxy]tetrahydropyran-3,4,5-triol
DA-58220
SMR000156227
CS-0009856
NS00023810
C01533
4-O-(beta-D-glucosyl)-trans-4-sinapyl alcohol
Q891785
ELEUTHEROSIDE B (CONSTITUENT OF ELEUTHERO) [DSC]
Eleutheroside B, United States Pharmacopeia (USP) Reference Standard
(E)-4-[-3-Hydroxy-1-propenyl]-2,6-dimethoxyphenyl-beta-D-glucopyranoside
.beta.-D-Glucopyranoside, 4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenyl
2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
4-((1E)-3-HYDROXY-1-PROPEN-1-YL)-2,6-DIMETHOXYPHENYL-.BETA.-D-GLUCOPYRANOSIDE
I(2)-D-Glucopyranoside, 4-[(1E)-3-hydroxy-1-propen-1-yl]-2,6-dimethoxyphenyl
- Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
- Abd Ellah AE, Mohamed KM, et al. (2014). Cinnamyl alcohol, benzyl alcohol, and flavonoid glycosides from Sanchezia nobilis. Chemistry of Natural Compounds,2014,50(5),823-826. [View]
- Mohamed KM (2001). Phenylpropanoid glucosides from Chrozophora obliqua. Phytochemistry,2001,58,615-618. [View] [PubMed]
- Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]
Pubchem:
5316860
Cas:
118-34-3
Gnps:
CCMSLIB00006405304
Zinc:
ZINC000003779261
Kegg Ligand:
C01533
Chebi:
9380
Nmrshiftdb2:
60022276
Metabolights:
MTBLC9380
Chembl:
CHEMBL250872
Comptox:
DTXSID2042438
Bindingdb:
50241356
CPRiL:
101362
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 372.37 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 372.37 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 372.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.34
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.77
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.34
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 59.61
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.08
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.42
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.09
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.47
- 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
- -4.38
- Rat (Acute)
- 2.06
- Rat (Chronic Oral)
- 3.62
- Fathead Minnow
- 4.08
- 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
- 459.54
- Hydration Free Energy
- -15.12
- Log(D) at pH=7.4
- -0.13
- Log(P)
- -1.14
- Log S
- -1.87
- Log(Vapor Pressure)
- -10.35
- Melting Point
- 162.94
- pKa Acid
- 7.09
- pKa Basic
- 2.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9178 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9178 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8376 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8376 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8131 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8131 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8110 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8110 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8070 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8070 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7875 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7875 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7698 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7698 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 3 | 0.7631 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 3 | 0.7631 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7607 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7607 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7512 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7512 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7499 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7499 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7450 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7450 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7421 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7421 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7413 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7413 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7402 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7402 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7331 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7331 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7248 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7248 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 3 | 0.7242 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 3 | 0.7242 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7212 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7212 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7171 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7171 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7148 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7148 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7140 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7140 |
| Metallophosphoesterase | A3DJ38 | A3DJ38_HUNT2 | Clostridium thermocellum | 2 | 0.7112 |
| Metallophosphoesterase | A3DJ38 | A3DJ38_HUNT2 | Clostridium thermocellum | 2 | 0.7112 |
| Methyltransferase type 12 | Q88JU2 | Q88JU2_PSEPK | Pseudomonas putida | 3 | 0.7014 |
| Methyltransferase type 12 | Q88JU2 | Q88JU2_PSEPK | Pseudomonas putida | 3 | 0.7014 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7003 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7003 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7001 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7001 |