N-benzylhexadecanamide: isolated from Lepidium meyenii; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
N-benzylhexadecanamide : A macamide resulting from the formal condensation of the carboxy group of hexadecanoic acid with benzylamine. A moderate inhibitor of fatty acid amide hydrolase. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Lepidium | genus | A plant genus of the family BRASSICACEAE growing in Peru mountains. It is the source of maca root.[MeSH] | Brassicaceae | A plant family of the order Capparales, subclass Dilleniidae, class Magnoliopsida. They are mostly herbaceous plants with peppery-flavored leaves, due to gluconapin (GLUCOSINOLATES) and its hydrolysis product butenylisotrhiocyanate. The family includes many plants of economic importance that have been extensively altered and domesticated by humans. Flowers have 4 petals. Podlike fruits contain a number of seeds. Cress is a general term used for many in the Brassicacea family. Rockcress is usually ARABIS; Bittercress is usually CARDAMINE; Yellowcress is usually RORIPPA; Pennycress is usually THLASPI; Watercress refers to NASTURTIUM; or RORIPPA or TROPAEOLUM; Gardencress refers to LEPIDIUM; Indiancress refers to TROPAEOLUM.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 11198769 |
| CHEMBL ID | 2415102 |
| CHEBI ID | 140849 |
| SCHEMBL ID | 2166861 |
| MeSH ID | M0418431 |
| Synonym |
|---|
| n-benzylhexadecanamide |
| CHEBI:140849 , |
| n-(phenylmethyl)-hexadecanamide |
| macamide 1 |
| 74058-71-2 |
| n-benzylpalmitamide |
| AKOS002676451 |
| hexadecanamide, n-(phenylmethyl)- |
| chembl2415102 , |
| bdbm50438776 |
| SCHEMBL2166861 |
| n-hexadecanoyl benzylamine |
| LMFA08020155 |
| MLGPKWUKOQAAGI-UHFFFAOYSA-N |
| unii-1m5uvs8juu |
| AC-34557 |
| 1M5UVS8JUU , |
| hexadecanamide, n-benzyl- |
| DTXSID50458532 |
| macamide b |
| mfcd00378779 |
| n-benzyl hexadecanamide |
| n-benzylhexadecanamide;macamide 1 |
| CS-0022546 |
| HY-N2365 |
| FT-0775820 |
| Q27252600 |
| MS-25310 |
| macamideb |
| Role | Description |
|---|---|
| neuroprotective agent | Any compound that can be used for the treatment of neurodegenerative disorders. |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor | An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of fatty acid amide hydrolase (EC 3.5.1.99). |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| secondary carboxamide | A carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1). |
| macamide | A fatty amide resulting from the formal condensation of a fatty acid with benzylamine or a substituted (commonly 3-methoxy-) benzylamine. The term originally referred to bioactive and marker compounds isolated from maca (Lepidium meyenii, a herb cultivated for centuries by the indigenous people in the Peruvian Andes as a staple food crop) but is now also used to refer to synthetic analogues. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Fatty-acid amide hydrolase 1 | Homo sapiens (human) | IC50 (µMol) | 500.0000 | 0.0002 | 0.5982 | 7.0000 | AID765038 |
| Bifunctional epoxide hydrolase 2 | Homo sapiens (human) | IC50 (µMol) | 0.5240 | 0.0000 | 0.5450 | 9.1000 | AID1684614 |
| Bifunctional epoxide hydrolase 2 | Mus musculus (house mouse) | IC50 (µMol) | 0.4220 | 0.0017 | 0.0567 | 0.4220 | AID1684612 |
| Bifunctional epoxide hydrolase 2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.3700 | 0.0060 | 0.0980 | 0.3700 | AID1684613 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| endoplasmic reticulum membrane | Fatty-acid amide hydrolase 1 | Homo sapiens (human) |
| cytoskeleton | Fatty-acid amide hydrolase 1 | Homo sapiens (human) |
| organelle membrane | Fatty-acid amide hydrolase 1 | Homo sapiens (human) |
| peroxisome | Bifunctional epoxide hydrolase 2 | Homo sapiens (human) |
| peroxisomal matrix | Bifunctional epoxide hydrolase 2 | Homo sapiens (human) |
| cytosol | Bifunctional epoxide hydrolase 2 | Homo sapiens (human) |
| extracellular exosome | Bifunctional epoxide hydrolase 2 | Homo sapiens (human) |
| peroxisome | Bifunctional epoxide hydrolase 2 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1695710 | Cytotoxicity against human THP-1 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay | 2020 | RSC medicinal chemistry, Oct-01, Volume: 11, Issue:10 | Synthesis and biological screening of a library of macamides as TNF-α inhibitors. |
| AID1189981 | Antiproliferative activity against human PC3 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID765038 | Inhibition of human recombinant FAAH using N-arachidonyl-7-amino-4-methylcoumarin as substrate preincubated for 20 mins before substrate addition by fluorescence assay | 2013 | Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17 | Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition. |
| AID1189978 | Antiproliferative activity against human NCI/ADR-RES cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID1684613 | Inhibition of recombinant rat sEH expressed in baculovirus expression system using MNPC as substrate by fluorescence-based assay | |||
| AID1189979 | Antiproliferative activity against human 786-0 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID1189982 | Antiproliferative activity against human OVCAR3 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID1684614 | Inhibition of recombinant human sEH expressed in baculovirus expression system using MNPC as substrate by fluorescence-based assay | |||
| AID1684612 | Inhibition of recombinant mouse sEH expressed in baculovirus expression system using MNPC as substrate by fluorescence-based assay | |||
| AID1695711 | Inhibition of LPS-induced TNFalpha production in human THP-1 cells incubated for 2 hrs followed by LPS stimulation and measured after 12 hrs by ELISA | 2020 | RSC medicinal chemistry, Oct-01, Volume: 11, Issue:10 | Synthesis and biological screening of a library of macamides as TNF-α inhibitors. |
| AID1189983 | Cytotoxicity against human HaCaT cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID1189977 | Antiproliferative activity against human MCF7 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID1189980 | Antiproliferative activity against human NCI-H460 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID765035 | Inhibition of human recombinant FAAH using N-arachidonyl-7-amino-4-methylcoumarin as substrate preincubated at 500 uM for 20 mins before substrate addition by fluorescence assay | 2013 | Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17 | Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition. |
| AID1189976 | Antiproliferative activity against human U251 cells assessed as tumor growth inhibition after 48 hrs by sulforhodamine B assay | 2015 | Bioorganic & medicinal chemistry, Jan-15, Volume: 23, Issue:2 | Antiproliferative activity of synthetic fatty acid amides from renewable resources. |
| AID765036 | Inhibition of human recombinant FAAH using N-arachidonyl-7-amino-4-methylcoumarin as substrate preincubated at 10 uM for 20 mins before substrate addition by fluorescence assay | 2013 | Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17 | Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (12.50) | 29.6817 |
| 2010's | 4 (50.00) | 24.3611 |
| 2020's | 3 (37.50) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (13.05) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||