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Record Information
Version2.0
Created at2022-09-08 19:55:14 UTC
Updated at2022-09-08 19:55:14 UTC
NP-MRD IDNP0273030
Secondary Accession NumbersNone
Natural Product Identification
Common Namehexadecenoate
DescriptionPalmitelaidic acid, also known as trans-palmitoleate or (9E)-9-hexadecenoate, 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. Palmitelaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Palmitelaidic acid has been detected, but not quantified in, milk (cow). This could make palmitelaidic acid a potential biomarker for the consumption of these foods. hexadecenoate is found in Agaricus blazei, Agelas conifera, Allamanda cathartica, Amphimedon compressa, Aplysina lacunosa, Arnica montana, Cervicornia cuspidifera, Curcuma longa, Homo sapiens, Juniperus phoenicea, Myrmekioderma rea, Proiphys amboinensis, Pseudo-nitzschia multistriata, Salpa thompsoni, Tripneustes ventricosus and Xestospongia muta. hexadecenoate was first documented in 2000 (PMID: 11026624). Additional sources are animal and dairy fats and partly hydrogenated fish oils.
Structure
Thumb
Synonyms
Chemical FormulaC16H30O2
Average Mass254.4082 Da
Monoisotopic Mass254.22458 Da
IUPAC Name(9E)-hexadec-9-enoic acid
Traditional Nametrans-palmitoleic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012328
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028947
KNApSAcK IDNot Available
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
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1007/s11745-000-0614-y. [PubMed:11026624 ]
  2. LOTUS database [Link]