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Capsaicin; Nonanoyl analogue

AlkaPlorer ID: AK002776

Synonym: N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, N-Vanillylnonanamide, Synthetic capsaicin, Pseudocapsaicin, Pelargonoyl vanillylamide, Nonivamide, PSVA, FEMA 2787, HH 50, AH 23491X, 8-Nordihydrocapsaicin 

IUPAC Name: N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide

Structure

SMILES: CCCCCCCCC(O)=NCC1=CC=C(O)C(OC)=C1

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InChI: InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

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InChIKey: RGOVYLWUIBMPGK-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 293.40700000000004

TPSA？: 62.05000000000001

MolLogP？: 4.607900000000004

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
Bacteria Cell membrane Activity nan None 10.1021/acs.jmedchem.2c01604
Cavia porcellus Cavia porcellus EC50 400.0 nM 10.1021/jm00068a014
Cavia porcellus Cavia porcellus EC50 400.0 nM 10.1021/jm00068a015
Equus caballus Ferritin light chain Potency 28183.8 nM None
Escherichia coli Escherichia coli MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
Escherichia coli K-12 Endonuclease 4 Potency 707.9 nM None
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 22387.2 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 25118.9 nM None
Homo sapiens Arachidonate 15-lipoxygenase Potency 25118.9 nM None
Homo sapiens Bile acid receptor FXR Potency 25118.9 nM None
Homo sapiens Bloom syndrome protein Potency 50118.7 nM None
Homo sapiens Cytochrome P450 1A2 AC50 12589.25 nM None
Homo sapiens Cytochrome P450 2C19 AC50 7943.28 nM None
Homo sapiens Cytochrome P450 2C19 Potency 7943.3 nM None
Homo sapiens Cytochrome P450 2C9 AC50 3162.28 nM None
Homo sapiens Cytochrome P450 2C9 Potency 3162.3 nM None
Homo sapiens Cytochrome P450 2D6 AC50 25118.86 nM None
Homo sapiens Cytochrome P450 2D6 Potency 25118.9 nM None
Homo sapiens Cytochrome P450 3A4 AC50 3981.07 nM None
Homo sapiens Cytochrome P450 3A4 Potency 3981.1 nM None
Homo sapiens Cytochrome P450 3A4 Potency 25118.9 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 7.1 nM None
Homo sapiens DNA polymerase iota Potency 112201.8 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 10000.0 nM None
Homo sapiens HEK293 CC50 62.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
Homo sapiens Histone deacetylase 6 Inhibition 26.52 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 58.83 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 25118.9 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 89125.1 nM None
Homo sapiens Peripheral myelin protein 22 Potency 8492.1 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 23715.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 33498.3 nM None
Homo sapiens Vanilloid receptor Activity nan None 10.1021/jm030560j
Homo sapiens Vanilloid receptor Potency 10.3 nM None
Homo sapiens Vanilloid receptor Potency 162.9 nM None
Klebsiella pneumoniae Klebsiella pneumoniae MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
Mus musculus Mus musculus ED50 5.0 umol.kg-1 10.1021/jm00068a014
Mus musculus Mus musculus ED50 5.0 umol.kg-1 10.1021/jm00068a015
Mus musculus Mus musculus Inhibition 72.3 % 10.1021/jm00070a002
Mus musculus Mus musculus Latency 31.2 None 10.1021/jm00070a002
Mus musculus Mus musculus Lethality 50.0 % 10.1021/jm00070a002
Mus musculus Mus musculus Response 8.0 None 10.1021/jm00070a002
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 1584.9 nM None
Rattus norvegicus Rattus norvegicus Analgesia 17.0 % 10.1021/jm00070a002
Rattus norvegicus Rattus norvegicus BP -28.3 mmHg 10.1021/jm00033a011
Rattus norvegicus Rattus norvegicus DOSE 0.005 mg.kg-1 10.1021/jm00033a011
Rattus norvegicus Rattus norvegicus EC50 550.0 nM 10.1021/jm00068a014
Rattus norvegicus Vanilloid receptor EC50 223.0 nM 10.1016/j.bmcl.2012.06.059
Rattus norvegicus Vanilloid receptor EC50 550.0 nM 10.1021/jm00068a015
Rattus norvegicus Vanilloid receptor EC50 550.0 nM 10.1021/jm00068a016
Rattus norvegicus Vanilloid receptor EC50 550.0 nM 10.1021/jm960139d
Rattus norvegicus Vanilloid receptor Ki 1223.0 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 4.409 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.2361 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.01 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 6.32 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
None NON-PROTEIN TARGET Potency 3162.3 nM None
None NON-PROTEIN TARGET Potency 15848.9 nM None
None NON-PROTEIN TARGET Potency 17782.8 nM None
None Unchecked Ac50 0.7943 uM None
None Unchecked Ac50 2.239 uM None
None Unchecked AC50 794.3 nM None
None Unchecked AC50 2238.7 nM None
None Unchecked CC50 59.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
None Unchecked HC5 200.0 ug ml-1 10.1021/acs.jmedchem.2c01604
None Unchecked HC50 200.0 ug ml-1 10.1021/acs.jmedchem.2c01604
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked MIC 50.0 ug.mL-1 10.1021/acs.jmedchem.2c01604
None Unchecked Potency 6309.6 nM None

Metabolism Information