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Human Metabolome Database Version 3.5

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Showing metabocard for Hexacosanoic acid (HMDB02356)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:49 -0600
Update Date 2013-02-08 17:11:48 -0700
HMDB ID HMDB02356
Secondary Accession Numbers None
Metabolite Identification
Common Name Hexacosanoic acid
Description X-linked adrenoleukodystrophy (X-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. (PMID 16750542 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Cerate
  2. Ceratinate
  3. Ceratinic acid
  4. Ceric acid
  5. Cerinate
  6. Cerinic acid
  7. Cerotic acid
  8. Cerylate
  9. Cerylic acid
  10. Hexacosanoate
  11. Hexacosanoate (N-C26:0)
  12. Hexacosanoic acid
  13. N-Hexacosanoate
  14. N-Hexacosanoic acid
Chemical Formula C26H52O2
Average Molecular Weight 396.6899
Monoisotopic Molecular Weight 396.396730908
IUPAC Name hexacosanoic acid
Traditional IUPAC Name hexacosanoic acid
CAS Registry Number 506-46-7
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 Key XMHIUKTWLZUKEX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Straight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight chain fatty acids(Lipidmaps)
  • straight-chain saturated fatty acid(ChEBI)
  • very long-chain fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Straight Chain Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 88.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.810E-05 g/L ALOGPS
LogP 9.87 ALOGPS
LogP 10.7 ChemAxon
LogS -7.34 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 24 ChemAxon
Refractivity 123.09 ChemAxon
Polarizability 55.83 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Adrenal Gland
Pathways
Name SMPDB Link KEGG Link
Beta Oxidation of Very Long Chain Fatty Acids SMP00052 map01040 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.110 +/- 0.006 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.83 +/- 0.45 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.88 (0.25-1.5) uM Adult (>18 years old) Both Neonatal adrenoleukodystrophy Not Available
Blood Detected and Quantified
Article_icon
8.8 (2.5-15.0) uM Adult (>18 years old) Both Adrenoleukodystrophy Not Available
Blood Detected and Quantified
Article_icon
2.0 (2.0-2.09) uM Adult (>18 years old) Both Peroxisomal disorder Not Available
Blood Detected and Quantified
Article_icon
4.10 (2.42 - 6.43) uM Adult (>18 years old) Both Adrenomyeloneuropathy Not Available
Associated Disorders and Diseases
Disease References
Adrenomyeloneuropathy
  • Sadeghi-Nejad A, Senior B: Adrenomyeloneuropathy presenting as Addison's disease in childhood. N Engl J Med. 1990 Jan 4;322(1):13-6. Pubmed: 2294415 Link_out
    Adrenoleukodystrophy, neonatal
      • http://www.metagene.de/program/d.prg?mp=ADRENOLEUKODYSTROPHY,%20NEONATAL
      Adrenoleukodystrophy
        • http://www.metagene.de/program/d.prg?mp=ADRENOLEUKODYSTROPHY,%20NEONATAL
        Peroxisomal disorders, new type, liver
          • http://www.metagene.de/program/d.prg?mp=PEROXISOMAL%20DISORDERS,%20NEW%20TYPE,%20LIVER
          Associated OMIM IDs
          DrugBank ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB003045
          KNApSAcK ID C00035114 Link_out
          Chemspider ID 10037 Link_out
          KEGG Compound ID Not Available
          BioCyc ID 2-PG Link_out
          BiGG ID 1459812 Link_out
          Wikipedia Link Cerate Link_out
          NuGOwiki Link HMDB02356 Link_out
          Metagene Link HMDB02356 Link_out
          METLIN ID 6642 Link_out
          PubChem Compound 10469 Link_out
          PDB ID Not Available
          ChEBI ID 31009 Link_out
          References
          Synthesis Reference Tsuji S; Sano T; Ariga T; Miyatake T Increased synthesis of hexacosanoic acid (C23:0) by cultured skin fibroblasts from patients with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). Journal of biochemistry (1981), 90(4), 1233-6.
          Material Safety Data Sheet (MSDS) Download (PDF)
          General References
          1. Moser HW, Moser AB, Powers JM, Nitowsky HM, Schaumburg HH, Norum RA, Migeon BR: The prenatal diagnosis of adrenoleukodystrophy. Demonstration of increased hexacosanoic acid levels in cultured amniocytes and fetal adrenal gland. Pediatr Res. 1982 Mar;16(3):172-5. Pubmed: 7063272 Link_out
          2. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8. Pubmed: 15565636 Link_out
          Enzymes
          Name: Long-chain-fatty-acid--CoA ligase 1
          Reactions:
            Gene Name: ACSL1
            Uniprot ID: P33121 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA