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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:24:03 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060482
Secondary Accession Numbers
  • HMDB60482
Metabolite Identification
Common NameHexadecenal
DescriptionAmong the 19 human ALDHs, ALDH3A2 is the only known ALDH that catalyzes the oxidation of long-chain fatty aldehydes including C16 aldehydes (hexadecanal and trans-2-hexadecenal) generated through sphingolipid metabolism. (PMID: 23721920 ) We recently identified that two products within the sphingolipid pathway, sphingosine-1-PO4 and hexadecenal, directly regulate BAK and BAX activation, respectively. (PMID: 23750296 ) Sphingosine-1-phosphate lyase (SPL) is the only known enzyme that irreversibly cleaves sphingosine-1-phosphate (S1P) into phosphoethanolamine and (2E)-hexadecenal during the final step of sphingolipid catabolism. (PMID: 22444536 ) Sphingosine 1-phosphate, a bioactive signaling molecule with diverse cellular functions, is irreversibly degraded by the endoplasmic reticulum enzyme sphingosine 1-phosphate lyase, generating trans-2-hexadecenal and phosphoethanolamine. We recently demonstrated that trans-2-hexadecenal causes cytoskeletal reorganization, detachment, and apoptosis in multiple cell types via a JNK-dependent pathway. (PMID: 22727907 )
Structure
Data?1563866066
Synonyms
ValueSource
(2E)-HexadecenalChEBI
2-trans-HexadecenalChEBI
(2E)-Hexadec-2-enalHMDB
2-(D5)-HexadecenalHMDB
2-(15,15,16,16,16-D5)-HexadecenalHMDB
2-HexadecenalMeSH
Chemical FormulaC16H30O
Average Molecular Weight238.4088
Monoisotopic Molecular Weight238.229665582
IUPAC Name(2E)-hexadec-2-enal
Traditional Name2-trans-hexadecenal
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\C=O
InChI Identifier
InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h14-16H,2-13H2,1H3/b15-14+
InChI KeyKLJFYXOVGVXZKT-CCEZHUSRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty aldehydes
Direct ParentFatty aldehydes
Alternative Parents
Substituents
  • Fatty aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility5.6e-05 g/LALOGPS
logP6.97ALOGPS
logP6.1ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity77.25 m³·mol⁻¹ChemAxon
Polarizability32.52 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]+164.46631661259
DarkChem[M-H]-163.78831661259
DeepCCS[M+H]+167.73230932474
DeepCCS[M-H]-163.71230932474
DeepCCS[M-2H]-201.330932474
DeepCCS[M+Na]+176.96330932474
AllCCS[M+H]+166.432859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+169.532859911
AllCCS[M+Na]+170.432859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-169.732859911
AllCCS[M+HCOO]-171.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HexadecenalCCCCCCCCCCCCC\C=C\C=O2258.8Standard polar33892256
HexadecenalCCCCCCCCCCCCC\C=C\C=O1842.8Standard non polar33892256
HexadecenalCCCCCCCCCCCCC\C=C\C=O1875.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexadecenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-07im-9700000000-2c13204d06f7eb2717212017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexadecenal 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 - Hexadecenal 10V, Positive-QTOFsplash10-000i-0190000000-fd969cd7262af491d84d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 20V, Positive-QTOFsplash10-059i-7970000000-0d33189fbc54287fc6f12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 40V, Positive-QTOFsplash10-0a4l-9800000000-1d27dc6f4cbaa7f9fe162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 10V, Negative-QTOFsplash10-000i-0090000000-108c8ba671de7d698e9c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 20V, Negative-QTOFsplash10-052r-0090000000-9e187c8e1c3bcb512ec42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 40V, Negative-QTOFsplash10-052f-8970000000-e2bbec2b313129e521a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 10V, Positive-QTOFsplash10-05uj-9520000000-c5fcf67323e03a2ca0b02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 20V, Positive-QTOFsplash10-0a5a-9200000000-911dd1c303ce58c3deb62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 40V, Positive-QTOFsplash10-0a4m-9000000000-c2477e88688a37257f1d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 10V, Negative-QTOFsplash10-000i-0090000000-755d6a2b1ffd2f706c0b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 20V, Negative-QTOFsplash10-000i-0090000000-a540059de9ca8fde48be2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecenal 40V, Negative-QTOFsplash10-00y0-9720000000-1d971990b816f176c9af2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06123
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280541
PDB IDNot Available
ChEBI ID17585
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Kitamura T, Naganuma T, Abe K, Nakahara K, Ohno Y, Kihara A: Substrate specificity, plasma membrane localization, and lipid modification of the aldehyde dehydrogenase ALDH3B1. Biochim Biophys Acta. 2013 Aug;1831(8):1395-401. doi: 10.1016/j.bbalip.2013.05.007. Epub 2013 May 27. [PubMed:23721920 ]
  3. Renault TT, Chipuk JE: Inter-organellar communication with mitochondria regulates both the intrinsic and extrinsic pathways of apoptosis. Commun Integr Biol. 2013 Mar 1;6(2):e22872. doi: 10.4161/cib.22872. [PubMed:23750296 ]
  4. Luth A, Neuber C, Kleuser B: Novel methods for the quantification of (2E)-hexadecenal by liquid chromatography with detection by either ESI QTOF tandem mass spectrometry or fluorescence measurement. Anal Chim Acta. 2012 Apr 13;722:70-9. doi: 10.1016/j.aca.2012.01.063. Epub 2012 Feb 13. [PubMed:22444536 ]
  5. Upadhyaya P, Kumar A, Byun HS, Bittman R, Saba JD, Hecht SS: The sphingolipid degradation product trans-2-hexadecenal forms adducts with DNA. Biochem Biophys Res Commun. 2012 Jul 20;424(1):18-21. doi: 10.1016/j.bbrc.2012.06.012. Epub 2012 Jun 19. [PubMed:22727907 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:
SGPL1
Uniprot ID:
O95470
Molecular weight:
63523.265
Reactions
Sphingosine 1-phosphate → O-Phosphoethanolamine + Hexadecenaldetails