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(−)-syringaresinol-4,4′-bis-O-beta-d-glucopyranoside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Lignan Bis-Glucoside
| Canonical Smiles | OC[C@@H]1O[C@H](Oc2c(OC)cc(cc2OC)[C@@H]2OC[C@@H]3[C@H]2CO[C@H]3c2cc(OC)c(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C34H46O18/c1-43-17-5-13(6-18(44-2)31(17)51-33-27(41)25(39)23(37)21(9-35)49-33)29-15-11-48-30(16(15)12-47-29)14-7-19(45-3)32(20(8-14)46-4)52-34-28(42)26(40)24(38)22(10-36)50-34/h5-8,15-16,21-30,33-42H,9-12H2,1-4H3/t15-,16-,21-,22+,23-,24+,25+,26-,27-,28+,29+,30+,33+,34-/m1/s1 |
| InChIKey | FFDULTAFAQRACT-NCMGNBMTSA-N |
| Formula | C34H46O18 |
| HBA | 18 |
| HBD | 8 |
| MW | 742.72 |
| Rotatable Bonds | 12 |
| TPSA | 254.14 |
| LogP | -1.85 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 52 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 742.27 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium sinaicum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
(−)-syringaresinol-4,4′-bis-O-beta-d-glucopyranoside
- El Gamal A.A, Takeya K, et al. (1997). Lignan bis-glucosides from Galium sinaicum. Phytochemistry, 1997, 45(3), 597-600. [View]
Pubchem:
71600002
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(cc2)ccc2C(OC3)C(C34)COC4c5ccc(cc5)OC6CCCCO6
Level: 4
Mol. Weight: 742.72 g/mol
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccc(cc4)OC5CCCCO5
Level: 3
Mol. Weight: 742.72 g/mol
SMILES: C1OCC(C12)COC2c3ccc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 742.72 g/mol
SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4
Level: 2
Mol. Weight: 742.72 g/mol
SMILES: C1OCC(C12)COC2c3ccccc3
Level: 1
Mol. Weight: 742.72 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 742.72 g/mol
SMILES: C1OCC(C12)COC2
Level: 0
Mol. Weight: 742.72 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 742.72 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 742.72 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.42
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 3.680
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1236.76
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.820
- Plasma Protein Binding
- 76.95
- 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
- 4.110
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -28.630
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.380
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.250
- 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
- -2244114.650
- Rat (Acute)
- 2.770
- Rat (Chronic Oral)
- 5.030
- Fathead Minnow
- 2839.410
- 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
- 247623.450
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.370
- Log(P)
- -1.94
- Log S
- -3.61
- Log(Vapor Pressure)
- -8071.99
- Melting Point
- 235.24
- pKa Acid
- -26.4
- pKa Basic
- 0.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8940 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.8784 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8735 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8361 |
| UDP-3-O-acyl-N-acetylglucosamine deacetylase | O67648 | LPXC_AQUAE | Aquifex aeolicus | 3 | 0.8333 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8299 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8102 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7683 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7663 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7500 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7461 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7422 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7387 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7382 |
| Beta-lactamase | Q79MP6 | Q79MP6_PSEAI | Pseudomonas aeruginosa | 2 | 0.7342 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7323 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7242 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7235 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7230 |
| Type IV pilus retractation ATPase PilT | P24559 | PILT_PSEAE | Pseudomonas aeruginosa | 3 | 0.7196 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7161 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7153 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7130 |
| Protein RecA | Q59560 | RECA_MYCS2 | Mycolicibacterium smegmatis155) | 4 | 0.7104 |
| Beta-glucosidase 12 | B8AVF0 | BGL12_ORYSI | Oryza sativa subsp. indica | 3 | 0.7090 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7089 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7036 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7034 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7034 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7032 |