Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:22:08 UTC
Update Date2021-10-13 05:34:45 UTC
HMDB IDHMDB0012273
Secondary Accession Numbers
  • HMDB12273
Metabolite Identification
Common NamePalmitic amide
DescriptionPalmitic amide is a primary fatty acid amide coming from Palmitic acid (C16:0). Primary fatty acid amides (R-CO-NH2) is a class of compounds that have only recently been isolated and characterized from biological sources. Key questions remain regarding how these lipid amides are produced and degraded in biological systems. (PMID 15282088 ). Fatty acid amides lies in the competition with endocannabinoids for binding to the active site of the enzyme and thus in increasing the concentration of endocannabinoids, by preventing their degradation.It can be used as a marker of disease in subjects, e.g. first-onset, drug-naive patients; the disease may be, for example, schizophrenia, paranoid schizophrenia or an affective disorder.The metabolic network of primary fatty acid amides is more severely altered in affective disorder than in first onset, paranoid schizophrenia.
Structure
Data?1582753036
Synonyms
ValueSource
Amide 16ChEBI
Cetyl amideChEBI
PalmitamideChEBI
Amide HPLHMDB
HexadecanamideHMDB
N-HexadecanamideHMDB
Palmitamide (acd/name 4.0)HMDB
Palmitic acid amideHMDB
Palmityl amideHMDB
Palmitic amideChEBI
Chemical FormulaC16H33NO
Average Molecular Weight255.4393
Monoisotopic Molecular Weight255.256214683
IUPAC Namehexadecanamide
Traditional Namecetamide
CAS Registry Number629-54-9
SMILES
CCCCCCCCCCCCCCCC(N)=O
InChI Identifier
InChI=1S/C16H33NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H2,17,18)
InChI KeyHSEMFIZWXHQJAE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentFatty amides
Alternative Parents
Substituents
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point107.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point392.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.29 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.200 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP10(6.59) g/LALOGPS
logP10(5.45) g/LChemAxon
logS10(-6.1) g/LALOGPS
pKa (Strongest Acidic)16.88ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.91 m³·mol⁻¹ChemAxon
Polarizability34.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.33431661259
DarkChem[M-H]-167.73231661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Palmitic amide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-598f492c2cd776499b4c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Palmitic amide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 10V, Positive-QTOFsplash10-0a4r-0090000000-3c9f141c75066a2398922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 20V, Positive-QTOFsplash10-000i-3490000000-e6606289d705029001b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 40V, Positive-QTOFsplash10-052f-9500000000-07907a7380a4835de91f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 10V, Negative-QTOFsplash10-0udi-0090000000-890f7bbcaaf1db47945d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 20V, Negative-QTOFsplash10-0udi-4090000000-82ac387d22ca75f672422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 40V, Negative-QTOFsplash10-0006-9000000000-debec9f69c4564bc98db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 10V, Positive-QTOFsplash10-0a4i-2090000000-e0be3fd37dbd248724dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 20V, Positive-QTOFsplash10-0a4i-9330000000-85bbd73ab27ae78eb8122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 40V, Positive-QTOFsplash10-0a4l-9000000000-34946d94faa688e18efc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 10V, Negative-QTOFsplash10-0udi-0090000000-4554907a5632f4ee99fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 20V, Negative-QTOFsplash10-0006-9040000000-a03004303f9e9bc316dc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitic amide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011671
KNApSAcK IDC00037269
Chemspider ID62629
KEGG Compound IDNot Available
BioCyc IDCPD6666-3
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69421
PDB IDNot Available
ChEBI ID74475
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1634641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Carpenter T, Poore DD, Gee AJ, Deshpande P, Merkler DJ, Johnson ME: Use of reversed phase HP liquid chromatography to assay conversion of N-acylglycines to primary fatty acid amides by peptidylglycine-alpha-amidating monooxygenase. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 25;809(1):15-21. [PubMed:15282088 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.