Compounds > hexadecanamide
Page last updated: 2024-12-06

hexadecanamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hexadecanamide, also known as palmitamide, is a long-chain fatty acid amide naturally occurring in mammals. It is synthesized from palmitic acid, a saturated fatty acid, and is involved in various physiological processes. Research suggests that hexadecanamide plays a role in regulating appetite, sleep, and inflammation. It has also been found to exhibit anti-inflammatory and analgesic properties. Studies on hexadecanamide focus on understanding its role in biological systems, its potential therapeutic applications, and its interactions with other molecules. Its importance lies in its potential to be developed as a drug for treating conditions such as obesity, insomnia, and chronic pain.'

hexadecanamide : A fatty amide that is the carboxamide derived from palmitic acid. [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]

Cross-References

ID SourceID
PubMed CID69421
CHEMBL ID32605
CHEBI ID74475
SCHEMBL ID43384
SCHEMBL ID23571900
MeSH IDM0062252

Synonyms (39)

Synonym
AKOS015839800
cetyl amide
amide hpl
palmitic acid amide
palmitamide
nsc3327
palmitic amide
629-54-9
n-hexadecanamide
palmityl amide
nsc-3327
amide 16
hexadecanamide
NCGC00161182-02
chebi:74475 ,
CHEMBL32605
hexadecanoic acid amide
H0067
LMFA08010009
nsc 3327
unii-qx1mq82m73
einecs 211-095-5
qx1mq82m73 ,
FT-0626967
palmitamide [inci]
palmitamide (palmitic acid amide)
SCHEMBL43384
HSEMFIZWXHQJAE-UHFFFAOYSA-N
DTXSID8044707
c16h33no
mfcd00025534
palmitamide (acd/name 4.0)
Q18651888
2,6-dichloro-4-nitropyridine?
AS-56522
bdbm50463964
SCHEMBL23571900
CS-0081845
SY038954
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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]

Drug Classes (1)

ClassDescription
primary fatty amideA primary carboxamide RC(=O)NH2 resultng from the formal condensation of the carboxy group of a fatty acid with ammonia.
[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 Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency7.07950.003245.467312,589.2998AID2517
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily V member 2Rattus norvegicus (Norway rat)IC50 (µMol)10.00000.03701.93458.6000AID1400243; AID1400244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID49296Percent inhibition of specific binding of [3H]CP-55940 towards human cannabinoid receptor 1 from Chinese hamster ovary cell membranes at the concentration of 10 uM2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Modifications of the ethanolamine head in N-palmitoylethanolamine: synthesis and evaluation of new agents interfering with the metabolism of anandamide.
AID195691Inhibition of [3H]- AEA metabolism (N-arachidonoylethanolamine) in rat brain homogenates using [3H]anandamide as the labeled substrate.2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Modifications of the ethanolamine head in N-palmitoylethanolamine: synthesis and evaluation of new agents interfering with the metabolism of anandamide.
AID49691Percent inhibition of specific binding of [3H]WIN-55212-2 towards human cannabinoid receptor 2 from Chinese hamster ovary cell membranes at the concentration of 10 uM2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Modifications of the ethanolamine head in N-palmitoylethanolamine: synthesis and evaluation of new agents interfering with the metabolism of anandamide.
AID387967Antiproliferative activity against human WI38 cells at 10 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation.
AID387968Antiproliferative activity against mouse RAW264.7 cells at 10 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation.
AID195561Percent inhibition of AEA (N-arachidonoylethanolamine) metabolism in rat brain homogenates using [3H]anandamide as the labeled substrate.2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Modifications of the ethanolamine head in N-palmitoylethanolamine: synthesis and evaluation of new agents interfering with the metabolism of anandamide.
AID71618Relative rate of fatty acid amide hydrolase hydrolysis of compound compared to that of oleamide.2000Bioorganic & medicinal chemistry letters, Dec-04, Volume: 10, Issue:23
Fatty acid amide hydrolase substrate specificity.
AID1400244Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of CBD-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
AID1400243Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of LPC-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (8.33)18.7374
1990's0 (0.00)18.2507
2000's3 (25.00)29.6817
2010's4 (33.33)24.3611
2020's4 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.20

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.20 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.09 (4.65)
Search Engine Demand Index40.31 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		2.0710monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
ethanolamine
[no description available]		2.0710ethanolamines;
primary alcohol;
primary amine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		2.6320long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
2-aminoethoxydiphenyl borate
2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.		2.1710organoboron compound;
primary amino compound		calcium channel blocker;
IP3 receptor antagonist;
potassium channel opener
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		2.0410aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
palmidrol
palmidrol: a cannabinoid receptor-inactive eCB-related molecule used as prophylactic in helping to prevent respiratory viral infection. palmitoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid.		2.7430endocannabinoid;
N-(long-chain-acyl)ethanolamine;
N-(saturated fatty acyl)ethanolamine		anti-inflammatory drug;
anticonvulsant;
antihypertensive agent;
neuroprotective agent
caprolactam
Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.		2.0710caprolactamshuman blood serum metabolite
arachidic acid
icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.		2.1710long-chain fatty acid;
straight-chain saturated fatty acid		plant metabolite
zirconium
Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.		2.3110titanium group element atom
stearoylethanolamide
N-(octadecanoyl)ethanolamine : An N-acylethanolamine 18:0 that is the ethanolamide of octadecanoic acid.		2.1710N-acylethanolamine 18:0
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.0710benzenes;
phenyl acetates
n-palmitoylglycine
N-hexadecanoylglycine : An N-acylglycine in which the acyl group is specified as hexadecanoyl (palmitoyl).		2.0410fatty amide;
N-acylglycine 16:0		human metabolite;
marine metabolite
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.1710icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
oleic acid
Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.		2.1710octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
ammonium acetate
ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.		2.0710acetate salt;
ammonium salt		buffer;
food acidity regulator
lenabasum
lenabasum: a CB2 cannabinoid receptor agonist; structure in first source		2.0410
erucic acid
[no description available]		2.1710docosenoic acid
anandamide
anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.		2.7430endocannabinoid;
N-acylethanolamine 20:4		human blood serum metabolite;
neurotransmitter;
vasodilator agent
arachidonyl dopamine
arachidonyl dopamine: a ligand for the vanilloid receptor VR1		2.0410catechols;
fatty amide;
N-(fatty acyl)-dopamine;
secondary carboxamide
n-oleoyldopamine
N-oleoyldopamine: putative capsaicin receptor ligand; produces hyperalgesia; isolated from the brain. N-oleoyldopamine : A fatty amide resulting from the formal condensation of the carboxy group of oleic acid with the amino group of dopamine. Synthesised in catecholaminergic neurons, it crosses the blood-brain barrier and might be considered as a carrier of dopamine into the brain. It is a transient receptor potential vanilloid type 1 (TRPV1) receptor agonist.		2.0410catechols;
fatty amide;
N-(fatty acyl)-dopamine;
secondary carboxamide		TRPV1 agonist
homo-gamma-linolenylethanolamide
homo-gamma-linolenylethanolamide: found in brain; binds to the cannabinoid receptor; RN given for (Z,Z,Z)-isomer; structure given in first source		2.0410N-acylethanolamine 20:3
7,10,13,16-docosatetraenylethanolamide
7,10,13,16-docosatetraenylethanolamide: found in brain; binds to the cannabinoid receptor; structure given in first source; RN given refers to (ALL-Z)-isomer		2.0410N-acylethanolamine 22:4
oleylamide
oleylamide: plastic additive; can cause contact urticaria; RN given refers to (Z)-isomer; a sleep inducing factor. aliphatic amide : A carboxamide in which the amide linkage is bonded directly to an aliphatic system.. oleamide : A fatty amide derived from oleic acid.		3.1650primary fatty amidehuman metabolite;
plant metabolite
n-arachidonylglycine
N-arachidonylglycine: structure in first source. N-arachidonoylglycine : Biologically active derivative of anandamide		2.0410fatty amide;
N-acylglycine
arachidonoyl amine
arachidonoyl amine : A primary fatty amide resulting from the formal condensation of the carboxy group of arachidonic acid with ammonia.		2.0410primary fatty amidecannabinoid receptor agonist
linoleoyl ethanolamide
linoleoyl ethanolamide: RN given for (Z,Z)-isomer. linoleoyl ethanolamide : An N-acylethanolamine 18:2 that is the ethanolamide of linoleic acid.		2.4920N-acylethanolamine 18:2EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor
N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine
synaptamide: structurally similar to the endocannabinoid N-arachidonoylethanolamine (anandamide). N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine : An N-acylethanolamine 22:6 that is the ethanolamide of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid.		2.1710endocannabinoid;
N-acylethanolamine 22:6
n-oleoylethanolamine
N-oleoylethanolamine: ceramidase inhibitor. oleoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide.		2.4920endocannabinoid;
N-(long-chain-acyl)ethanolamine;
N-acylethanolamine 18:1		EC 3.5.1.23 (ceramidase) inhibitor;
geroprotector;
PPARalpha agonist
olvanil
[no description available]		2.1710methoxybenzenes;
phenols
erucyl amide
erucyl amide: RN given refers to (Z)-isomer. erucamide : A primary fatty amide resulting from the formal condensation of the carboxy group of erucic acid with ammonia. It is commonly used as a slip additive in the plastic manufacturing industry.		2.171013-docosenamideEC 3.1.1.7 (acetylcholinesterase) inhibitor;
human metabolite;
mammalian metabolite;
plant metabolite;
rat metabolite
linoleamide
linoleamide: C18-H33-N-O. linoleamide : A fatty amide obtained from linoleic acid.		2.5220primary fatty amidehuman metabolite
n-arachidonoylalanine
N-arachidonoylalanine: inhibits fatty acid amide hydrolase; structure in first source. N-arachidonoyl-L-alanine : An N-acyl-L-alanine resulting from the formal condensation of the amino group of L-alanine with the carboxy group of arachidonic acid.		2.0410N-(fatty acyl)-L-alpha-amino acid;
N-acyl-L-alanine		mammalian metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Mastitis
INFLAMMATION of the BREAST, or MAMMARY GLAND.		07.610
Acute Confusional Senile Dementia
[description not available]		02.2510
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.2510
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.0710
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0710