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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:30:15 UTC
Update Date2022-03-07 02:56:24 UTC
HMDB IDHMDB0039954
Secondary Accession Numbers
  • HMDB39954
Metabolite Identification
Common NameMacamide B
DescriptionMacamide B belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, macamide b is considered to be a fatty amide. Based on a literature review a small amount of articles have been published on Macamide B.
Structure
Data?1563863467
Synonyms
ValueSource
Macamide 1ChEBI
N-(Phenylmethyl)-hexadecanamideChEBI
N-BenzylpalmitamideChEBI
N-BenzylhexadecanamideHMDB, MeSH
Chemical FormulaC23H39NO
Average Molecular Weight345.5619
Monoisotopic Molecular Weight345.303164875
IUPAC NameN-benzylhexadecanamide
Traditional NameN-benzylhexadecanamide
CAS Registry Number74058-71-2
SMILES
CCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C1
InChI Identifier
InChI=1S/C23H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-23(25)24-21-22-18-15-14-16-19-22/h14-16,18-19H,2-13,17,20-21H2,1H3,(H,24,25)
InChI KeyMLGPKWUKOQAAGI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • Benzenoid
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Secondary 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
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.5e-05 g/LALOGPS
logP6.3ALOGPS
logP7.4ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)16.04ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity108.42 m³·mol⁻¹ChemAxon
Polarizability45.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.11231661259
DarkChem[M-H]-191.94831661259
DeepCCS[M+H]+192.62330932474
DeepCCS[M-H]-190.07330932474
DeepCCS[M-2H]-223.27830932474
DeepCCS[M+Na]+198.96630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Macamide BCCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C13272.1Standard polar33892256
Macamide BCCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C12809.0Standard non polar33892256
Macamide BCCCCCCCCCCCCCCCC(=O)NCC1=CC=CC=C12897.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Macamide B,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)N(CC1=CC=CC=C1)[Si](C)(C)C2803.9Semi standard non polar33892256
Macamide B,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)N(CC1=CC=CC=C1)[Si](C)(C)C2723.4Standard non polar33892256
Macamide B,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C3064.4Semi standard non polar33892256
Macamide B,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2909.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Macamide B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9440000000-c8750b4360e2115b67b82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macamide B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macamide B 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 - Macamide B 10V, Positive-QTOFsplash10-0a4i-3914000000-c2666f3d52538fd74ff52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 20V, Positive-QTOFsplash10-0a4i-3910000000-97770dfdb2721cb5993c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 40V, Positive-QTOFsplash10-052f-9400000000-29478044d0aa09a6c9472016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 10V, Negative-QTOFsplash10-0006-0129000000-608f3c8b91491f46ceb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 20V, Negative-QTOFsplash10-0kbf-4798000000-a4254086cc42b2188b052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 40V, Negative-QTOFsplash10-0006-9220000000-05d1d71216aa437474e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 10V, Positive-QTOFsplash10-0002-1109000000-0a8912e012c3b7e69f802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 20V, Positive-QTOFsplash10-052g-9646000000-941dc7f70e8bace010522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 40V, Positive-QTOFsplash10-0006-9200000000-76eac38f5fe9412b67f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 10V, Negative-QTOFsplash10-0006-0009000000-ba83796456dc359f70f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 20V, Negative-QTOFsplash10-0006-1019000000-75e38d6c833c24d21c792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macamide B 40V, Negative-QTOFsplash10-002f-9500000000-8ad9131913cad146f23e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019617
KNApSAcK IDC00054026
Chemspider ID9373838
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11198769
PDB IDNot Available
ChEBI ID140849
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .