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Showing Compound Hexacosaenoic acid (FDB004035)

Record Information
Version1.0
Creation date2010-04-08 22:06:03 UTC
Update date2019-11-26 02:59:45 UTC
Primary IDFDB004035
Secondary Accession Numbers
  • FDB003045
Chemical Information
FooDB NameHexacosaenoic acid
DescriptionHexacosanoic acid, also known as N-hexacosanoate or c26:0, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, hexacosanoic acid is considered to be a fatty acid lipid molecule. Hexacosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hexacosanoic acid can be found in a number of food items such as dandelion, potato, cottonseed, and sugar apple, which makes hexacosanoic acid a potential biomarker for the consumption of these food products. Hexacosanoic acid can be found primarily in blood, as well as in human adrenal gland and fibroblasts tissues. Hexacosanoic acid exists in all eukaryotes, ranging from yeast to humans. In humans, hexacosanoic acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Hexacosanoic acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Moreover, hexacosanoic acid is found to be associated with adrenomyeloneuropathy, peroxisomal biogenesis defect, and adrenoleukodystrophy, neonatal. Hexacosanoic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. [In the chem box it is shown folded only because of lack of space. In fact, it is a straight-chain, saturated fatty acid.] . Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary treatment is with Lorenzo's oil. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Adrenal insufficiency in ALD patients can be successfully treated (T3DB).
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
C26:0ChEBI
Ceratinic acidChEBI
Ceric acidChEBI
Cerinic acidChEBI
Cerotic acidChEBI
Cerotinic acidChEBI
Cerylic acidChEBI
CH3-[CH2]24-COOHChEBI
HexacosansaeureChEBI
Hexacosoic acidChEBI
Hexaeicosanoic acidChEBI
N-C26:0ChEBI
N-Hexacosanoic acidChEBI
CeratinateGenerator
CerateGenerator
CerinateGenerator
CerotateGenerator
CerotinateGenerator
CerylateGenerator
HexacosoateGenerator
HexaeicosanoateGenerator
N-HexacosanoateGenerator
HexacosanoateGenerator
Hexacosanoate (N-C26:0)HMDB
Hexacosanoic acidPhytoBank
FA(26:0)PhytoBank
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP9.87ALOGPS
logP10.7ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity123.09 m³·mol⁻¹ChemAxon
Polarizability55.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H52O2
IUPAC namehexacosanoic acid
InChI IdentifierInChI=1S/C26H52O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(27)28/h2-25H2,1H3,(H,27,28)
InChI KeyXMHIUKTWLZUKEX-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight396.6899
Monoisotopic Molecular Weight396.396730908
Classification
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0597-9201000000-41113a5b904c5db7332d2014-09-20View Spectrum
GC-MSHexacosanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2900100000-dc0324482e5853e76290Spectrum
GC-MSHexacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2900100000-dc0324482e5853e76290Spectrum
GC-MSHexacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2900100000-dc0324482e5853e76290Spectrum
GC-MSHexacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-9d83fa08f63878dd9794Spectrum
Predicted GC-MSHexacosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-8890000000-a358b076f9e4d3b08976Spectrum
Predicted GC-MSHexacosanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmr-9550000000-f90d4cc6a83ff8e16245Spectrum
Predicted GC-MSHexacosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4j-0109000000-bc2c74027165503fd92f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0pb9-2193000000-cf0ac4a96f99022c7b3a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w30-6096000000-65025824de97c5fb5ff72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-00lr-0009000000-998e2947790abd467bc72020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0009000000-bd3c909a0431684b20e72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug1-3439000000-ca5336c838aa140696262016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-6974000000-93ebd8f603ed3f48dd9d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-50e9c7751bdac41b78c82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0009000000-fdc9aa019c323235312e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-af814ec2317a697df1a02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-87ff11014d638fb7aedd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1009000000-28b98f74e9fa6d052c382021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9003000000-9b4d6e9900769e9411a52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2009000000-459e9bac675c0081de3d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-7039000000-16142145274003e6395d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-33f6f730f4cbdee5a9752021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDHEXACOSAENOIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).