Np mrd loader

Record Information
Version2.0
Created at2022-04-28 20:42:04 UTC
Updated at2022-04-28 20:42:04 UTC
NP-MRD IDNP0075413
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexadecanamide
DescriptionPalmitic amide, also known as hexadecanamide or amide 16, 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. Thus, palmitic amide is considered to be a fatty amide lipid molecule. Palmitic amide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Palmitic amide has been detected, but not quantified in, pomes. This could make palmitic amide a potential biomarker for the consumption of these foods. 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. 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. The metabolic network of primary fatty acid amides is more severely altered in affective disorder than in first onset, paranoid schizophrenia. Hexadecanamide is found in Averrhoa bilimbi , Boronella koniambiensis, Campylobacter jejuni, Cannabis sativa, Casimiroa edulis , Equisetum telmateia, Pseudo-nitzschia multistriata, Rhizoclonium hieroglyphicum and Zingiber officinale. Hexadecanamide was first documented in 1977 (PMID: 15064). Palmitic amide is a primary fatty acid amide coming from Palmitic acid (C16:0).
Structure
Thumb
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 Mass255.4393 Da
Monoisotopic Mass255.25621 Da
IUPAC Namehexadecanamide
Traditional Namecetamide
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Averrhoa bilimbiPlant
Bison bisonFooDB
Boronella koniambiensisPlant
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Campylobacter jejuniLOTUS Database
Cannabis sativaLOTUS Database
Capra aegagrus hircusFooDB
Casimiroa edulisPlant
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equisetum telmateiaLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pseudo-nitzschia multistriataLOTUS Database
Rhizoclonium hieroglyphicumViridiplantae
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zingiber officinaleLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.59ALOGPS
logP5.45ChemAxon
logS-6.1ALOGPS
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
HMDB IDHMDB0012273
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. Smith RN, Jones LV, Brennan JS, Vaughan CG: Identification of hexadecanamide in cannabis resin. J Pharm Pharmacol. 1977 Feb;29(2):126-7. doi: 10.1111/j.2042-7158.1977.tb11266.x. [PubMed:15064 ]