Capsaicin; (Z)-isomer
AlkaPlorer ID: AK291599
Synonym: Zucapsaicin
IUPAC Name: (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Structure
SMILES: COC1=CC(CN=C(O)CCCC/C=C\C(C)C)=CC=C1O
InChI: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-
InChIKey: YKPUWZUDDOIDPM-VURMDHGXSA-N
Reference
Separation and Quantification of Capsaicinoids Using Complexation Chromatography
PubChem CID: 1548942
CAS: 25775-90-0
LOTUS: LTS0082685
SuperNatural Ⅲ: SN0452959-02
NPASS: NPC308885
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 |
| Heliopsis longipes | Heliopsis | Asteraceae | Asterales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 305.418
TPSA？: 62.05
MolLogP？: 4.629900000000005
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 | Inhibition | 26.82 | % | 10.6019/CHEMBL4513141 |
| Bacillus anthracis | Anthrax lethal factor | Potency | 6309.6 | nM | None |
| Bacillus anthracis | Anthrax lethal factor | Potency | 15848.9 | nM | None |
| Candida albicans | Candida albicans | Inhibition | 4.72 | % | 10.6019/CHEMBL4513141 |
| Cryptococcus neoformans | Cryptococcus neoformans | Inhibition | -5.9 | % | 10.6019/CHEMBL4513141 |
| Escherichia coli | Escherichia coli | Inhibition | 0.0 | % | 10.6019/CHEMBL4513141 |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 3548.1 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 22387.2 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 25118.9 | nM | None |
| Homo sapiens | Caspase-1 | Potency | 15848.9 | nM | None |
| Homo sapiens | Cellular tumor antigen p53 | Potency | 31622.8 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 1584.89 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 3162.28 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | 6309.57 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | 7943.28 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 6309.6 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 7943.3 | nM | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 10000.0 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | 316.23 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | 1258.93 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | 1995.26 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 316.2 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 1258.9 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 1995.3 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 3981.1 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | 6309.57 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | 15848.93 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 6309.6 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | Potency | 15848.9 | 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 | AC50 | 7943.28 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 3981.1 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 7943.3 | nM | None |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 44668.4 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 39810.7 | nM | None |
| Homo sapiens | Lysosomal alpha-glucosidase | Potency | 14125.4 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 29855.4 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 33498.3 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 35481.3 | nM | None |
| Homo sapiens | Vanilloid receptor | EC50 | 28.2 | nM | 10.1021/acs.jmedchem.9b01046 |
| Homo sapiens | Vanilloid receptor | Ki | 1080.0 | nM | 10.1021/acs.jmedchem.9b01046 |
| Klebsiella pneumoniae | Klebsiella pneumoniae | Inhibition | 12.92 | % | 10.6019/CHEMBL4513141 |
| Mus musculus | Mus musculus | Inhibition | 79.5 | % | 10.1021/jm00070a002 |
| Mus musculus | Mus musculus | Latency | 39.9 | None | 10.1021/jm00070a002 |
| Mus musculus | Mus musculus | Lethality | 50.0 | % | 10.1021/jm00070a002 |
| Mus musculus | Mus musculus | Response | 6.0 | None | 10.1021/jm00070a002 |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Inhibition | 15.26 | % | 10.6019/CHEMBL4513141 |
| Rattus norvegicus | Rattus norvegicus | Analgesia | 0.0 | % | 10.1021/jm00070a002 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 12.44 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | -0.17 | % | 10.6019/CHEMBL4495565 |
| Staphylococcus aureus | Staphylococcus aureus | Inhibition | 14.17 | % | 10.6019/CHEMBL4513141 |
| Trypanosoma cruzi | Cruzipain | Potency | 39810.7 | nM | None |
| None | Unchecked | Potency | 14125.4 | nM | None |
| None | Unchecked | Potency | 22387.2 | nM | None |
| None | Unchecked | Potency | 28183.8 | nM | None |