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(7S,8R,8′R)-(-)-lariciresinol 4−4'-bis-O-D-glucoside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Lignan Glycoside
| Canonical Smiles | OC[C@@H]1O[C@H](Oc2ccc(cc2OC)C[C@@]2(C)CO[C@@H]([C@@]2(C)CO)c2ccc(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/C34H48O16/c1-33(11-16-5-7-18(20(9-16)44-3)47-31-28(42)26(40)24(38)22(12-35)49-31)15-46-30(34(33,2)14-37)17-6-8-19(21(10-17)45-4)48-32-29(43)27(41)25(39)23(13-36)50-32/h5-10,22-32,35-43H,11-15H2,1-4H3/t22-,23+,24-,25+,26+,27-,28-,29+,30+,31-,32+,33-,34+/m0/s1 |
| InChIKey | XCVRVMCUDQOZGV-NBJKAXQBSA-N |
| Formula | C34H48O16 |
| HBA | 16 |
| HBD | 9 |
| MW | 712.74 |
| Rotatable Bonds | 12 |
| TPSA | 246.68 |
| LogP | -1.62 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 50 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 712.29 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium brunneum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
(7S,8R,8′R)-(-)-lariciresinol 4−4'-bis-O-D-glucoside
- Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(cc2)ccc2CC3CC(OC3)c4ccc(cc4)OC5CCCCO5
Level: 4
Mol. Weight: 712.74 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 712.74 g/mol
SMILES: c1ccccc1C(OC2)CC2Cc3ccc(cc3)OC4CCCCO4
Level: 3
Mol. Weight: 712.74 g/mol
SMILES: C1OCCC1Cc2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 712.74 g/mol
SMILES: O1CCCC1c2ccc(cc2)OC3CCCCO3
Level: 2
Mol. Weight: 712.74 g/mol
SMILES: c1ccccc1CC2CC(OC2)c3ccccc3
Level: 2
Mol. Weight: 712.74 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 712.74 g/mol
SMILES: C1OCCC1Cc2ccccc2
Level: 1
Mol. Weight: 712.74 g/mol
SMILES: O1CCCC1c2ccccc2
Level: 1
Mol. Weight: 712.74 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 712.74 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 712.74 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 712.74 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.52
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -3.740
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 247.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.940
- Plasma Protein Binding
- 85.86
- 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
- 4.270
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.280
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.460
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.660
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -448948.500
- Rat (Acute)
- 2.970
- Rat (Chronic Oral)
- 4.890
- Fathead Minnow
- 577.830
- 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
- 45015.020
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 0.640
- Log(P)
- -1.67
- Log S
- -3.39
- Log(Vapor Pressure)
- -1449.89
- Melting Point
- 249.35
- pKa Acid
- 3.32
- pKa Basic
- 3.18
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8778 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8324 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8322 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8297 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8248 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8060 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7904 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7790 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7701 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7700 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7611 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7590 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7432 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7387 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7384 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7307 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7153 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7051 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7018 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7001 |