Showing metabocard for Palmitelaidic acid (LMDB00575)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:52:52 UTC
Update Date2016-07-20 21:02:08 UTC
LmdbLMDB00575
Secondary Accession NumbersNone
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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8910000000-20fcd1fc2d9e095b2c24Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9630000000-7eda678c0ecd65b2e479Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0093020000-3713e3e16e9fc8ff9d4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0090000000-15955555bad036fe5887Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090000000-dc1afa2b2526cfadca3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-dc1afa2b2526cfadca3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-1590300110-1fd83ca98726c802644eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03xr-9100000000-753b931fdaad64d31b10Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-9100000000-95d9bf8269a7484bde2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udi-0090000000-ba595d75ac5ffd8e39a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-0090000000-6798051e8e1a3c6902b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03xu-9400000000-97d42bdb3850c52e063bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0190000000-b90e88fd05f27a8c6a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-8890000000-9443f26541262f6a5367Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-48491c01799873ccfd89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-66b803b008379629bb01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1090000000-14c3fbae6fab6e807e87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9320000000-9d124393fa8133067dd9Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0012328
FooDB IDFDB028947
Phenol Explorer IDNot Available
KNApSAcK IDC00052377
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445872
ChEBI ID59265
PubChem Compound ID5282745
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [9734731 ]
  2. 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. [11026624 ]