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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:04 UTC
HMDB IDHMDB0000583
Secondary Accession Numbers
  • HMDB00583
Metabolite Identification
Common NameDocosanamide
DescriptionDocosanamide, also known as behenamide, 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, docosanamide is considered to be a fatty amide. Based on a literature review a significant number of articles have been published on Docosanamide.
Structure
Data?1582752141
Synonyms
ValueSource
BehenamideHMDB
Behenic acid amideHMDB
Behenic amideHMDB
BehenylamideHMDB
Chemical FormulaC22H45NO
Average Molecular Weight339.5988
Monoisotopic Molecular Weight339.350115067
IUPAC Namedocosanamide
Traditional Namebehenamide
CAS Registry Number3061-75-4
SMILES
CCCCCCCCCCCCCCCCCCCCCC(N)=O
InChI Identifier
InChI=1S/C22H45NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H2,23,24)
InChI KeyORAWFNKFUWGRJG-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point110 - 113 °CNot Available
Boiling Point471.12 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00029 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.329 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP9.15ALOGPS
logP8.12ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)16.88ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity106.51 m³·mol⁻¹ChemAxon
Polarizability47.63 ųChemAxon
Number of Rings0ChemAxon
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]+191.831661259
DarkChem[M-H]-192.16431661259
AllCCS[M+H]+203.15432859911
AllCCS[M-H]-192.6232859911
DeepCCS[M+H]+193.07230932474
DeepCCS[M-H]-189.35530932474
DeepCCS[M-2H]-225.59830932474
DeepCCS[M+Na]+201.88730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DocosanamideCCCCCCCCCCCCCCCCCCCCCC(N)=O3772.5Standard polar33892256
DocosanamideCCCCCCCCCCCCCCCCCCCCCC(N)=O2735.1Standard non polar33892256
DocosanamideCCCCCCCCCCCCCCCCCCCCCC(N)=O2807.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C2836.4Semi standard non polar33892256
Docosanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C2733.7Standard non polar33892256
Docosanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C2963.1Standard polar33892256
Docosanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2971.3Semi standard non polar33892256
Docosanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2887.3Standard non polar33892256
Docosanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2761.5Standard polar33892256
Docosanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C(C)(C)C3025.0Semi standard non polar33892256
Docosanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C(C)(C)C2938.4Standard non polar33892256
Docosanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C(C)(C)C3000.6Standard polar33892256
Docosanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3398.3Semi standard non polar33892256
Docosanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3207.6Standard non polar33892256
Docosanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2966.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosanamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9780000000-2e9365899b245c25c6a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosanamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosanamide 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 - Docosanamide 10V, Positive-QTOFsplash10-006x-0019000000-e08ec8abb87f590adbaf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 20V, Positive-QTOFsplash10-00di-3569000000-6795fc54dfaff10f0e222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 40V, Positive-QTOFsplash10-052f-7960000000-20225e25812ed3ec5c052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 10V, Negative-QTOFsplash10-000i-0009000000-c9cab6c3ce1e2dda926d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 20V, Negative-QTOFsplash10-000l-5029000000-58c604b1d86e4cf7315d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 40V, Negative-QTOFsplash10-0006-9000000000-2f8ebf6363213a9f20942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 10V, Positive-QTOFsplash10-0006-2009000000-dc2a0b726e3adca1a0492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 20V, Positive-QTOFsplash10-0596-9037000000-05d45aa71b09eee5c3dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 40V, Positive-QTOFsplash10-0a4l-9000000000-3a2028429d1b2fab33ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 10V, Negative-QTOFsplash10-000i-0009000000-441ed6bf73e3a5fc5b7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 20V, Negative-QTOFsplash10-0006-9004000000-da66ea2df9347ec28f8f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosanamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
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 IDFDB022129
KNApSAcK IDNot Available
Chemspider ID68940
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5565
PubChem Compound76468
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1364661
References
Synthesis ReferenceLong-chain aliphatic amides. (1963), 3 pp. GB 939378 19631016 CAN 60:30544 AN 1964:30544
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]