N-(4-Hydroxy-3-methoxybenzyl)-9-octadecenamide; (Z)-form
AlkaPlorer ID: AK301367
Synonym: Olvanil, N-Vanillyloleamide, NE 19550
IUPAC Name: (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]octadec-9-enamide
Structure
SMILES: CCCCCCCC/C=C\CCCCCCCC(O)=NCC1=CC=C(O)C(OC)=C1
InChI: InChI=1S/C26H43NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26(29)27-22-23-19-20-24(28)25(21-23)30-2/h10-11,19-21,28H,3-9,12-18,22H2,1-2H3,(H,27,29)/b11-10-
InChIKey: OPZKBPQVWDSATI-KHPPLWFESA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Capsicum | Solanaceae | Solanales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| Capsicum annuum | Capsicum | Solanaceae | Solanales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 417.63400000000007
TPSA？: 62.05000000000001
MolLogP？: 7.89480000000001
Number of H-Donors: 2
Number of H-Acceptors: 3
RingCount: 1
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Bacillus anthracis | Anthrax lethal factor | Potency | 25118.9 | nM | None |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 25118.9 | nM | None |
| Homo sapiens | Cellular tumor antigen p53 | Potency | 31622.8 | nM | None |
| Homo sapiens | Cerebroside-sulfatase | Potency | 21331.3 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 19952.62 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | 3162.28 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 3162.3 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | AC50 | 10000.0 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 10000.0 | nM | None |
| Homo sapiens | DMS-114 | IC50 | 50000.0 | nM | 10.1021/acs.jmedchem.0c01679 |
| Homo sapiens | DNA polymerase kappa | Potency | 12589.3 | nM | None |
| Homo sapiens | DNA polymerase kappa | Potency | 33587.5 | nM | None |
| Homo sapiens | Dopamine D1 receptor | Potency | 1458.0 | nM | None |
| Homo sapiens | EFM-19 | IC50 | 700.0 | nM | 10.1021/acs.jmedchem.0c01679 |
| Homo sapiens | Fibroblast | Growth Rate | -0.71 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.53 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.68 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.83 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.91 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.97 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Flap endonuclease 1 | Potency | 21192.3 | nM | None |
| Homo sapiens | Geminin | Potency | 23715.0 | nM | None |
| Homo sapiens | Glucose transporter | Inhibition | 8.15 | % | 10.6019/CHEMBL3433997 |
| Homo sapiens | HaCaT | Activity | nan | None | 10.1016/j.bmc.2010.12.046 |
| Homo sapiens | HEK293 | Potency | 29081.0 | nM | None |
| Homo sapiens | HEK-293T | Growth Rate | -0.94 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | -0.75 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | -0.47 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | -0.25 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.7 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HepG2 | Inhibition | 0.0 | % | 10.1038/nature09107 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | -16.65 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | -8.59 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 | Potency | 125.9 | nM | None |
| Homo sapiens | MCF7 | IC50 | 1000.0 | nM | 10.1021/acs.jmedchem.0c01679 |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 39810.7 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 3548.1 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 15848.9 | nM | None |
| Homo sapiens | Serine/threonine-protein kinase mTOR | Potency | 1648.2 | nM | None |
| Homo sapiens | Serine/threonine-protein kinase mTOR | Potency | 13091.8 | nM | None |
| Homo sapiens | T47D | IC50 | 750.0 | nM | 10.1021/acs.jmedchem.0c01679 |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 3349.8 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 11885.6 | nM | None |
| Homo sapiens | U2OS | Growth Rate | 0.77 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.84 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.87 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.88 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.94 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 19952.6 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 39810.7 | nM | None |
| Homo sapiens | Vanilloid receptor | Activity | 0.01 | uM | 10.1038/nchembio0705-85 |
| Homo sapiens | Vanilloid receptor | EC50 | 0.5012 | nM | 10.1021/jm020844o |
| Homo sapiens | Vanilloid receptor | Response | 67.2 | % | 10.1021/jm020844o |
| Leishmania mexicana | Glucose transporter | Inhibition | 5.67 | % | 10.6019/CHEMBL3433997 |
| Mus musculus | Mus musculus | Dose | 0.1 | uM kg-1 | 10.1021/jm960512h |
| Mus musculus | Mus musculus | ED50 | 2.1 | umol.kg-1 | 10.1021/jm960512h |
| Mus musculus | Mus musculus | ED50 | 11.3 | umol.kg-1 | 10.1021/jm960512h |
| Mus musculus | Mus musculus | ED50 | 400.0 | umol.kg-1 | 10.1021/jm960512h |
| Mus musculus | RAW264.7 | Activity | nan | None | 10.1016/j.bmc.2010.12.046 |
| Plasmodium falciparum | Hexose transporter 1 | Inhibition | 7.4 | % | 10.6019/CHEMBL3433997 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 0.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 93.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Inhibition | 96.0 | % | 10.1038/nature09107 |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 16944.1 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | XC50 | 401.94 | nM | 10.1038/nature09107 |
| Rattus norvegicus | C6 | Activity | 95.0 | % | 10.1021/acs.jmedchem.0c01679 |
| Rattus norvegicus | Peripheral myelin protein 22 | Potency | 4547.9 | nM | None |
| Rattus norvegicus | Peripheral myelin protein 22 | Potency | 12579.7 | nM | None |
| Rattus norvegicus | Thioredoxin reductase 1, cytoplasmic | Potency | 354.8 | nM | None |
| Rattus norvegicus | Thioredoxin reductase 1, cytoplasmic | Potency | 15003.0 | nM | None |
| Rattus norvegicus | Thioredoxin reductase 1, cytoplasmic | Potency | 37685.8 | nM | None |
| Rattus norvegicus | Transient receptor potential cation channel subfamily V member 2 | IC50 | 160.0 | nM | 10.1021/acs.jmedchem.8b00734 |
| Rattus norvegicus | Transient receptor potential cation channel subfamily V member 2 | IC50 | 1700.0 | nM | 10.1021/acs.jmedchem.8b00734 |
| Rattus norvegicus | Transient receptor potential cation channel subfamily V member 2 | Inhibition | nan | % | 10.1021/acs.jmedchem.8b00734 |
| Rattus norvegicus | Vanilloid receptor | EC50 | 170.0 | nM | 10.1021/jm00068a016 |
| Rattus norvegicus | Vanilloid receptor | EC50 | 170.0 | nM | 10.1021/jm960512h |
| Rattus norvegicus | Vanilloid receptor | EC50 | 202.0 | nM | 10.1016/j.bmcl.2012.06.059 |
| Rattus norvegicus | Vanilloid receptor | Ki | 142.0 | nM | 10.1016/j.bmcl.2012.06.059 |
| Rattus norvegicus | Vanilloid receptor | Ki | nan | None | 10.1016/j.bmcl.2012.06.059 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 16.84 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | 0.15 | % | 10.6019/CHEMBL4495565 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | 26.8 | % | 10.21203/rs.3.rs-23951/v1 |
| None | ADMET | AUC | 0.1 | ug.hr/g | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | AUC | 8.0 | ug.hr/g | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | Drug metabolism | 24.0 | % | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | Drug metabolism | 74.0 | % | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | Drug metabolism | 90.0 | % | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | Drug uptake | 1.0 | % | 10.1021/acs.jmedchem.0c01679 |
| None | ADMET | Drug uptake | 4.0 | % | 10.1021/acs.jmedchem.0c01679 |
| None | Unchecked | Ac50 | 7.079 | uM | None |
| None | Unchecked | Ac50 | 25.12 | uM | None |
| None | Unchecked | AC50 | 7079.5 | nM | None |
| None | Unchecked | AC50 | 25118.9 | nM | None |
| None | Unchecked | Activity | 20.5 | % | 10.1021/acs.jmedchem.0c01679 |
| None | Unchecked | IFI | 4.38 | % | 10.1038/nature09107 |
| None | Unchecked | Potency | 20596.2 | nM | None |
| None | Unchecked | Potency | 28183.8 | nM | None |
| None | Unchecked | Potency | 31622.8 | nM | None |