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7S,8R,8′R-(−)-lariciresinol-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)c2ccc(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/C32H44O16/c1-42-20-8-14(3-5-18(20)45-31-28(40)26(38)24(36)22(11-34)47-31)7-16-13-44-30(17(16)10-33)15-4-6-19(21(9-15)43-2)46-32-29(41)27(39)25(37)23(12-35)48-32/h3-6,8-9,16-17,22-41H,7,10-13H2,1-2H3/t16-,17-,22?,23?,24-,25+,26?,27?,28+,29-,30+,31-,32+/m0/s1 |
| InChIKey | PBLWZMSRSJTRHJ-SCYUORAGSA-N |
| Formula | C32H44O16 |
| HBA | 16 |
| HBD | 9 |
| MW | 684.69 |
| Rotatable Bonds | 12 |
| TPSA | 246.68 |
| LogP | -2.4 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 48 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 684.26 |
| 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-(−)-lariciresinol-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: 684.69 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 684.69 g/mol
SMILES: c1ccccc1C(OC2)CC2Cc3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 684.69 g/mol
SMILES: C1OCCC1Cc2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 684.69 g/mol
SMILES: O1CCCC1c2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 684.69 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccccc3
Level: 2
Mol. Weight: 684.69 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 684.69 g/mol
SMILES: C1OCCC1Cc2ccccc2
Level: 1
Mol. Weight: 684.69 g/mol
SMILES: O1CCCC1c2ccccc2
Level: 1
Mol. Weight: 684.69 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 684.69 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 684.69 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 684.69 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.53
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.49
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 137.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.92
- Plasma Protein Binding
- 71.92
- 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
- 4.34
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.71
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.49
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.45
- 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
- -249663.91
- Rat (Acute)
- 2.91
- Rat (Chronic Oral)
- 4.91
- Fathead Minnow
- 327.68
- 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
- 22295.56
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 0.03
- Log(P)
- -2.18
- Log S
- -3.08
- Log(Vapor Pressure)
- -725.94
- Melting Point
- 233.61
- pKa Acid
- 4.33
- pKa Basic
- 3.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8993 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8779 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8520 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8496 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.8457 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.8449 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8378 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8217 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8204 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8110 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8078 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7954 |
| Protein UshA | P07024 | USHA_ECOLI | Escherichia coli | 3 | 0.7893 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7855 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7855 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7721 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7660 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7606 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7597 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7549 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7541 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7536 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7440 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7426 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7425 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7369 |
| DNA polymerase theta | O75417 | DPOLQ_HUMAN | Homo sapiens | 4 | 0.7368 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7357 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7347 |
| UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase | Q9WY79 | MURE_THEMA | Thermotoga maritima | 3 | 0.7282 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7247 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7242 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7178 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7103 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7078 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7058 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7036 |