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7S,8R,8′R-(−)-5-methoxylariciresinol-4,4′-bis-O-beta-d-glucopyranoside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Lignan Bis-Glucoside
| Canonical Smiles | OCC1O[C@H](Oc2ccc(cc2OC)C[C@H]2CO[C@@H]([C@H]2CO)c2cc(OC)c(c(c2)OC)O[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)[C@@H](C([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C33H46O17/c1-43-19-7-14(4-5-18(19)47-32-28(41)26(39)24(37)22(11-35)48-32)6-16-13-46-30(17(16)10-34)15-8-20(44-2)31(21(9-15)45-3)50-33-29(42)27(40)25(38)23(12-36)49-33/h4-5,7-9,16-17,22-30,32-42H,6,10-13H2,1-3H3/t16-,17-,22?,23?,24-,25+,26?,27?,28+,29-,30+,32-,33-/m0/s1 |
| InChIKey | FMRHEQINXVLPNS-VGHWAIBISA-N |
| Formula | C33H46O17 |
| HBA | 17 |
| HBD | 9 |
| MW | 714.71 |
| Rotatable Bonds | 13 |
| TPSA | 255.91 |
| LogP | -2.39 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 50 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.64 |
| Exact Mass | 714.27 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium sinaicum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
7S,8R,8′R-(−)-5-methoxylariciresinol-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]
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(cc2)ccc2CC3CC(OC3)c4ccc(cc4)OC5CCCCO5
Level: 4
Mol. Weight: 714.71 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 714.71 g/mol
SMILES: c1ccccc1C(OC2)CC2Cc3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 714.71 g/mol
SMILES: C1OCCC1Cc2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 714.71 g/mol
SMILES: O1CCCC1c2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 714.71 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccccc3
Level: 2
Mol. Weight: 714.71 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 714.71 g/mol
SMILES: C1OCCC1Cc2ccccc2
Level: 1
Mol. Weight: 714.71 g/mol
SMILES: O1CCCC1c2ccccc2
Level: 1
Mol. Weight: 714.71 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 714.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 714.71 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 714.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.5
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -3.13
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 338.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.88
- Plasma Protein Binding
- 66.64
- 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
- 4.29
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.36
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.47
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.81
- 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
- -614586.37
- Rat (Acute)
- 2.85
- Rat (Chronic Oral)
- 5.12
- Fathead Minnow
- 786.17
- 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
- 63735.66
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -0.28
- Log(P)
- -2.3
- Log S
- -3.24
- Log(Vapor Pressure)
- -2063.91
- Melting Point
- 226.02
- pKa Acid
- 1.49
- pKa Basic
- 2.5
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8391 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8275 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8257 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8257 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8249 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8203 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8126 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7836 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7703 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7696 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.7567 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7462 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7449 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7395 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7370 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7355 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7342 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7268 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7213 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.7158 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7157 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7142 |
| Acetylglutamate kinase | Q0ASS9 | Q0ASS9_MARMM | Maricaulis maris | 3 | 0.7077 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 3 | 0.7061 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7039 |