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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 05:23:29 UTC
Update Date2019-07-23 07:19:03 UTC
HMDB IDHMDB0062656
Secondary Accession Numbers
  • HMDB62656
Metabolite Identification
Common NameLinoleamide
DescriptionLinoleamide, also known as 9,12-Octadecadienamide or Linoleic acid amide, is classified as a member of the Fatty amides. Fatty amides are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Linoleamide is considered to be practically insoluble (in water) and relatively neutral. Linoleamide is a fatty amide lipid molecule
Structure
Data?1563866343
Synonyms
ValueSource
9,12-OctadecadienamideChEBI
Linoleic acid amideChEBI
Linoleoyl amideChEBI
Linoleate amideGenerator
(9Z,12Z)-Octadeca-9,12-dien-1-amideMeSH
Chemical FormulaC18H33NO
Average Molecular Weight279.468
Monoisotopic Molecular Weight279.256214687
IUPAC Name(9Z,12Z)-octadeca-9,12-dienimidic acid
Traditional Name(9Z,12Z)-octadeca-9,12-dienimidic acid
CAS Registry Number3072-13-7
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=N
InChI Identifier
InChI=1S/C18H33NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H2,19,20)/b7-6-,10-9-
InChI KeySFIHQZFZMWZOJV-HZJYTTRNSA-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0001 g/lALOGPS
LogP6.71ALOGPS
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(7.03) g/LALOGPS
logP10(3.79) g/LChemAxon
logS10(-6.2) g/LALOGPS
pKa (Strongest Acidic)0.31ChemAxon
pKa (Strongest Basic)13.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.08 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.28 m³·mol⁻¹ChemAxon
Polarizability36.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.76131661259
DarkChem[M-H]-178.20931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Linoleamide,1TMS,#1CCCCC/C=C\C/C=C\CCCCCCCC(=N)O[Si](C)(C)C2368.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Linoleamide,1TMS,#2CCCCC/C=C\C/C=C\CCCCCCCC(O)=N[Si](C)(C)C2356.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Linoleamide,1TBDMS,#1CCCCC/C=C\C/C=C\CCCCCCCC(=N)O[Si](C)(C)C(C)(C)C2626.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Linoleamide,1TBDMS,#2CCCCC/C=C\C/C=C\CCCCCCCC(O)=N[Si](C)(C)C(C)(C)C2615.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Linoleamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7930000000-ba4278ec42b9b46b98352017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoleamide GC-MS (1 TMS) - 70eV, Positivesplash10-01bi-7932000000-17765d909e40f65603502017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoleamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoleamide 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 - Linoleamide 10V, Positive-QTOFsplash10-01q9-0190000000-cdfe875ce3cc01a4ee802017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 20V, Positive-QTOFsplash10-03dr-3490000000-bf433b9c4757f7cd03bc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 40V, Positive-QTOFsplash10-000f-8910000000-d21aa47d864c4ebe98e22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 10V, Negative-QTOFsplash10-004i-0090000000-3be9c0addfd8a8ac11282017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 20V, Negative-QTOFsplash10-004l-3090000000-daf9eb9d6021ddd364de2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 40V, Negative-QTOFsplash10-0006-9000000000-ac5c646af0b3966c24662017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 10V, Positive-QTOFsplash10-001i-2490000000-463ccd06223121d7961f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 20V, Positive-QTOFsplash10-0089-8940000000-04524ab3820a7b08d60a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 40V, Positive-QTOFsplash10-05o4-9100000000-6621ba9eac9b350cecc52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 10V, Negative-QTOFsplash10-004i-0090000000-af3ddc4e5ed738c46a6c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 20V, Negative-QTOFsplash10-0006-9030000000-0bfc2578768dd64d1f5c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleamide 40V, Negative-QTOFsplash10-0006-9000000000-ab3043a29007f077b4462021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6435901
PDB IDNot Available
ChEBI ID82984
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.