Showing Compound Card for Hexacosanoic acid (CDB005780)

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Record Information
Version1.0
Created at2020-04-27 16:55:51 UTC
Updated at2021-01-04 18:49:16 UTC
CannabisDB IDCDB005780
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHexacosanoic acid
DescriptionHexacosanoic acid, also known as C26:0 or Cerotic acid, is a 26-carbon, long-chain saturated fatty acid. It 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. Hexacosanoic acid is a very hydrophobic molecule that is practically insoluble in water. It exists as a white or beige crystalline solid and is most commonly found in beeswax and carnauba wax. Hexacosanoic acid has also been detected, but not quantified, in peanuts. Hexacosanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, hexacosanoic acid is involved in beta oxidation of very long chain fatty acids. Hexacosanoic acid, with regard to humans, has been found to be associated with several diseases such as peroxisomal disorders, adrenomyeloneuropathy, and mental retardation, enteropathy, deafness, peripheral neuropathy, ichthyosis, and keratoderma. Hexacosanoic acid has also been linked to several inborn metabolic disorders including adrenoleukodystrophy (ALD) and peroxisomal biogenesis defect. ALD is characterized by normal development in early childhood, followed by rapid degeneration to a vegetative state. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Clinically, ALD is a heterogenous disorder, presenting with several distinct phenotypes, and no clear pattern of genotype-phenotype correlation. Treatment options for adrenoleukodystrophy (ALD) are limited. Adrenal insufficiency in ALD patients can be successfully treated. Approximately two-thirds of ALD patients will present with the childhood cerebral form of the disease, which is the most severe form. ALD is a peroxisomal disorder biochemically characterized by the accumulation of very long chain fatty acids (VLCFA), particularly hexacosanoic acid (C(26:0)) and tetracosanoic acid (C(24:0)), in tissues and biological fluids. The exact mechanism of the pathogenesis of the various forms of ALD is not known. Hexacosanoic acid is one of several acidic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC26H52O2
Average Molecular Weight396.69
Monoisotopic Molecular Weight396.3967
IUPAC Namehexacosanoic acid
Traditional Namehexacosanoic acid
CAS Registry Number506-46-7
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88.5 °CNot Available
Boiling Point250 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Long-chain-fatty-acid--CoA ligase 1ACSL14q35P33121 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002356
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004035
KNApSAcK IDC00035114
Chemspider ID10037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID1459812
Wikipedia LinkCerotic acid
METLIN ID6642
PubChem Compound10469
PDB IDNot Available
ChEBI ID31009
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Long-chain-fatty-acid--CoA ligase 1
General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:
ACSL1
Uniprot ID:
P33121
Molecular weight:
77942.685