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(+)-lyoniresinol
- Family: Plantae - Celastraceae
- Kingdom: Plantae
- Class: Lignan
| Canonical Smiles | OC[C@@H]1Cc2cc(OC)c(c(c2[C@@H]([C@H]1CO)c1cc(OC)c(c(c1)OC)O)OC)O |
|---|---|
| InChI | InChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/m0/s1 |
| InChIKey | ZDVZKBOFCHOPLM-SUNYJGFJSA-N |
| Formula | C22H28O8 |
| HBA | 8 |
| HBD | 4 |
| MW | 420.46 |
| Rotatable Bonds | 7 |
| TPSA | 117.84 |
| LogP | 2.04 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 420.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Maytenus senegalensis | Celastraceae | Plantae | 256095 |
Showing of synonyms
(+)-lyoniresinol
14464-90-5
CHEBI:68168
(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
CHEMBL455365
2,3-Naphthalenedimethanol, 1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-, (1S,2R,3R)-
(1S)-1alpha-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2beta,3alpha-
(1S,2R,3R)-1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-2,3-naphthalenedimethanol
Lyoniresinol, (+)-
HY-N3349
BDBM50242208
AKOS032962283
FL74077
DA-68978
FS-10365
CS-0023959
Q27136660
- Okoye FB, Agbo MO, et al. (2014). New neolignan glycoside and an unusual benzoyl malic acid derivative from Maytenus senegalensis leaves. Natural Product Research,2014,29,109-115. [View]
Pubchem:
11711453
Cas:
14464-90-5
Zinc:
ZINC000005410561
Chebi:
68168
Nmrshiftdb2:
60024971
Metabolights:
MTBLC68168
Chembl:
CHEMBL455365
Bindingdb:
50242208
No compound-protein relationship available.
SMILES: c1cccc(c12)CCCC2c3ccccc3
Level: 1
Mol. Weight: 420.46 g/mol
SMILES: C1CCCc(c12)cccc2
Level: 0
Mol. Weight: 420.46 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 420.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.65
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.250
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.880
- Plasma Protein Binding
- 72.44
- 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
- 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
- 16.320
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.120
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.990
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.030
- 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
- -25.840
- Rat (Acute)
- 2.140
- Rat (Chronic Oral)
- 3.350
- Fathead Minnow
- 4.160
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 476.400
- Hydration Free Energy
- -6.670
- Log(D) at pH=7.4
- 1.770
- Log(P)
- 0.34
- Log S
- -3.82
- Log(Vapor Pressure)
- -8.07
- Melting Point
- 168.72
- pKa Acid
- 7.71
- pKa Basic
- 3.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.9705 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9545 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.9034 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8641 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8620 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8611 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8535 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8462 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8326 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8227 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 5 | 0.8192 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8160 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8151 |
| Tubulin alpha chain | D0VWZ0 | D0VWZ0_SHEEP | Ovis aries | 3 | 0.8122 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8112 |
| 16S rRNA (adenine(1408)-N(1))-methyltransferase | A8C927 | NPMA_ECOLX | Escherichia coli | 4 | 0.8110 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8103 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7974 |
| chitinase | B0Y2Y2 | B0Y2Y2_ASPFC | Aspergillus fumigatus | 4 | 0.7936 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7894 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7877 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 4 | 0.7870 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7784 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7652 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 4 | 0.7626 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7625 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7597 |
| Deoxyribodipyrimidine photo-lyase | Q8PYK9 | Q8PYK9_METMA | Methanosarcina mazei | 5 | 0.7532 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7503 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7486 |
| Nucleoside permease | Q9KPL5 | Q9KPL5_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7460 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7459 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7450 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.7421 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7404 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7382 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7374 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7374 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7342 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7339 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7335 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7320 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7282 |
| PTS system glucose-specific EIIA component | P69783 | PTGA_ECOLI | Escherichia coli | 3 | 0.7264 |
| Catalase-peroxidase 2 | O59651 | KATG2_HALMA | Haloarcula marismortui | 3 | 0.7253 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7248 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7192 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7188 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7168 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7148 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7124 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 4 | 0.7094 |