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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:21:31 UTC
Update Date2022-03-07 02:55:37 UTC
HMDB IDHMDB0038073
Secondary Accession Numbers
  • HMDB38073
Metabolite Identification
Common NameOctadecyl fumarate
DescriptionOctadecyl fumarate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on Octadecyl fumarate.
Structure
Data?1563863136
Synonyms
ValueSource
Octadecyl fumaric acidGenerator
Monostearyl fumarateHMDB
Stearyl fumarateHMDB
Chemical FormulaC22H40O4
Average Molecular Weight368.5506
Monoisotopic Molecular Weight368.292659768
IUPAC Name(2Z)-4-(octadecyloxy)-4-oxobut-2-enoic acid
Traditional Name(2Z)-4-(octadecyloxy)-4-oxobut-2-enoic acid
CAS Registry Number1741-93-1
SMILES
CCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C22H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-26-22(25)19-18-21(23)24/h18-19H,2-17,20H2,1H3,(H,23,24)/b19-18-
InChI KeyMHQJUHSHQGQVTM-HNENSFHCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point93 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.7e-05 g/LALOGPS
logP8.3ALOGPS
logP7.89ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity107.66 m³·mol⁻¹ChemAxon
Polarizability47.44 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]+196.09231661259
DarkChem[M-H]-194.12531661259
DeepCCS[M+H]+195.27530932474
DeepCCS[M-H]-192.72530932474
DeepCCS[M-2H]-225.92730932474
DeepCCS[M+Na]+202.30330932474
AllCCS[M+H]+201.332859911
AllCCS[M+H-H2O]+198.932859911
AllCCS[M+NH4]+203.432859911
AllCCS[M+Na]+204.032859911
AllCCS[M-H]-196.632859911
AllCCS[M+Na-2H]-198.432859911
AllCCS[M+HCOO]-200.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Octadecyl fumarateCCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O4460.7Standard polar33892256
Octadecyl fumarateCCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O2673.9Standard non polar33892256
Octadecyl fumarateCCCCCCCCCCCCCCCCCCOC(=O)\C=C/C(O)=O2847.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octadecyl fumarate,1TMS,isomer #1CCCCCCCCCCCCCCCCCCOC(=O)/C=C\C(=O)O[Si](C)(C)C2871.8Semi standard non polar33892256
Octadecyl fumarate,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C3115.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Octadecyl fumarate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9240000000-c2fed47948322c9e2e8c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecyl fumarate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3941100000-a6499f91de3105d1e0182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecyl fumarate 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 - Octadecyl fumarate 10V, Positive-QTOFsplash10-0uxr-2029000000-1d8173844086573d8d4e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 20V, Positive-QTOFsplash10-0uk9-9385000000-cea678137dafef20f9202016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 40V, Positive-QTOFsplash10-0h2g-9760000000-aba0decbfcfb4436c8202016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 10V, Negative-QTOFsplash10-014j-6129000000-5e045accda5b9fda9b752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 20V, Negative-QTOFsplash10-014i-9433000000-d2927dab17102f0f06fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 40V, Negative-QTOFsplash10-0gi1-9120000000-7f29876802461f8a8b012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 10V, Negative-QTOFsplash10-014i-3209000000-a3045edbf1a111aab4b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 20V, Negative-QTOFsplash10-00xs-9111000000-ed27b22e151e594810072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 40V, Negative-QTOFsplash10-00di-9000000000-5355140fa15ef2e0093d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 10V, Positive-QTOFsplash10-0uxr-2398000000-b5c0ec3f8ca136581e352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 20V, Positive-QTOFsplash10-0uk9-8494000000-2465ca58d18251fa86292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecyl fumarate 40V, Positive-QTOFsplash10-05tb-9200000000-6ca71324f44adde6cd0e2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB017285
KNApSAcK IDNot Available
Chemspider ID4941511
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436905
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.