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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-06-03 20:33:59 UTC
Update Date2021-10-13 05:35:03 UTC
HMDB IDHMDB0012328
Secondary Accession Numbers
  • HMDB12328
Metabolite Identification
Common NamePalmitelaidic acid
DescriptionPalmitelaidic acid is a trans fatty acid (the trans isomer of palmitoleic acid). Trans fatty acids are known to cause changes in plasma lipids and lipoprotein phenotypes, but the mechanisms involved are unknown. The major dietary sources of trans fatty acids are partly hydrogenated vegetable oils, mainly elaidic acid (t-18:1D9). Additional sources are animal and dairy fats [palmitelaidic acid (t-16:1D9) and t-vaccenic acid (t-18:1D11)] and partly hydrogenated fish oils. (very-long-chain trans fatty acids, ie, >C22) (PMID: 9734731 ). Palmitelaidic acid has been reported as the predominant trans-16:1 isomer in cheeses made with goat and ewe milks (PMID: 11026624 ).
Structure
Data?1582753042
Synonyms
ValueSource
(9E)-Hexadecenoic acidChEBI
(e)-9-HexadecenoicacidChEBI
9-trans-Hexadecenoic acidChEBI
t-16:1D9ChEBI
t-9-Hexadecenoic acidChEBI
trans-9-Hexadecenoic acidChEBI
trans-Delta(9)-Hexadecenoic acidChEBI
trans-Palmitoleic acidChEBI
(9E)-HexadecenoateGenerator
9-trans-HexadecenoateGenerator
t-9-HexadecenoateGenerator
trans-9-HexadecenoateGenerator
trans-delta(9)-HexadecenoateGenerator
trans-Δ(9)-hexadecenoateGenerator
trans-Δ(9)-hexadecenoic acidGenerator
trans-PalmitoleateGenerator
PalmitelaidateGenerator
Palmitoleic acidMeSH
Palmitoleic acid, (Z)-isomerMeSH
Palmitoleic acid, sodium salt, (Z)-isomerMeSH
C16:1 trans-9MeSH
PalmitoleateMeSH
Palmitoleic acid, (e)-isomerMeSH
Palmitoleic acid, potassium salt, (Z)-isomerMeSH
(9E)-9-HexadecenoateHMDB
(9E)-9-Hexadecenoic acidHMDB
(e)-9-HexadecenoateHMDB
(e)-9-Hexadecenoic acidHMDB
(e)-Hexadec-9-enoateHMDB
(e)-Hexadec-9-enoic acidHMDB
trans-9-PalmitoleateGenerator
Palmitelaidic acidMeSH
Chemical FormulaC16H30O2
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
IUPAC Name(9E)-hexadec-9-enoic acid
Traditional Nametrans-palmitoleic acid
CAS Registry Number10030-73-6
SMILES
CCCCCC\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7+
InChI KeySECPZKHBENQXJG-BQYQJAHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point363.00 to 364.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.13 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.635 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP10(6.71) g/LALOGPS
logP10(5.89) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability33.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.20331661259
DarkChem[M-H]-170.30731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Palmitelaidic acid,1TMS,#1CCCCCC/C=C/CCCCCCCC(=O)O[Si](C)(C)C2021.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Palmitelaidic acid,1TBDMS,#1CCCCCC/C=C/CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2269.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Palmitelaidic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8910000000-20fcd1fc2d9e095b2c242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Palmitelaidic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9630000000-7eda678c0ecd65b2e4792017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Palmitelaidic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF , Negative-QTOFsplash10-004i-0093020000-3713e3e16e9fc8ff9d4e2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-0udi-0091010000-7210516a6de9436dfaef2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 20V, Negative-QTOFsplash10-0udi-0091010000-7210516a6de9436dfaef2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 30V, Negative-QTOFsplash10-0udi-1590500110-437a071e7d08786be6042017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF , Negative-QTOFsplash10-0udi-0090000000-15955555bad036fe58872017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-0udi-0091010000-7210516a6de9436dfaef2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 20V, Negative-QTOFsplash10-0udi-0090000000-dc1afa2b2526cfadca3b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 10V, Negative-QTOFsplash10-0udi-0090000000-e0fb9e9cfc066f8f82752017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid ESI-TOF 30V, Negative-QTOFsplash10-0udi-1590500110-437a071e7d08786be6042017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid LC-ESI-TOF , negative-QTOFsplash10-0udi-0090000000-dc1afa2b2526cfadca3b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid LC-ESI-TOF , negative-QTOFsplash10-0udi-0090000000-e0fb9e9cfc066f8f82752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid LC-ESI-TOF , negative-QTOFsplash10-0udi-1590500110-437a071e7d08786be6042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 10V, Positive-QTOFsplash10-0udi-0090000000-e0fb9e9cfc066f8f82752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 30V, Positive-QTOFsplash10-0udi-1590300110-1fd83ca98726c802644e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 90V, Negative-QTOFsplash10-03xr-9100000000-753b931fdaad64d31b102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 75V, Negative-QTOFsplash10-03di-9100000000-95d9bf8269a7484bde2b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 15V, Negative-QTOFsplash10-0udi-0090000000-ba595d75ac5ffd8e39a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 30V, Negative-QTOFsplash10-0udi-0090000000-6798051e8e1a3c6902b02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Palmitelaidic acid 60V, Negative-QTOFsplash10-03xu-9400000000-97d42bdb3850c52e063b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 10V, Positive-QTOFsplash10-0a4r-0190000000-b90e88fd05f27a8c6a112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 20V, Positive-QTOFsplash10-0a4i-8890000000-9443f26541262f6a53672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 40V, Positive-QTOFsplash10-052f-9600000000-48491c01799873ccfd892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 10V, Negative-QTOFsplash10-0udi-0090000000-66b803b008379629bb012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 20V, Negative-QTOFsplash10-0zfr-1090000000-14c3fbae6fab6e807e872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidic acid 40V, Negative-QTOFsplash10-0a4i-9320000000-9d124393fa8133067dd92016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.97 +/- 1.4 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028947
KNApSAcK IDC00052377
Chemspider ID4445872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282745
PDB IDNot Available
ChEBI ID59265
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1440291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mao YY, Bai JQ, Chen JH, Shou ZF, He Q, Wu JY, Chen Y, Cheng YY: A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation. Transpl Immunol. 2008 Apr;19(1):74-80. doi: 10.1016/j.trim.2008.01.006. Epub 2008 Feb 22. [PubMed:18346641 ]
  2. Hodgson JM, Wahlqvist ML, Boxall JA, Balazs ND: Platelet trans fatty acids in relation to angiographically assessed coronary artery disease. Atherosclerosis. 1996 Feb;120(1-2):147-54. [PubMed:8645355 ]
  3. Destaillats F, Wolff RL, Precht D, Molkentin J: Study of individual trans- and cis-16:1 isomers in cow, goat, and ewe cheese fats by gas-liquid chromatography with emphasis on the trans-delta3 isomer. Lipids. 2000 Sep;35(9):1027-32. [PubMed:11026624 ]
  4. van Greevenbroek MM, Robertus-Teunissen MG, Erkelens DW, de Bruin TW: Lipoprotein secretion by intestinal Caco-2 cells is affected differently by trans and cis unsaturated fatty acids: effect of carbon chain length and position of the double bond. Am J Clin Nutr. 1998 Sep;68(3):561-7. [PubMed:9734731 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.