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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:01:39 UTC
Update Date2019-07-23 06:29:53 UTC
HMDB IDHMDB0039540
Secondary Accession Numbers
  • HMDB39540
Metabolite Identification
Common NameCerebronic acid
DescriptionCerebronic acid, also known as cerebronsaeure or phrenosic acid, 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. Cerebronic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563863393
Synonyms
ValueSource
2-Hydroxy-tetracosansaeureChEBI
2-Hydroxylignoceric acidChEBI
2-Hydroxytetraeicosanoic acidChEBI
2-Hydroxytetraicosanoic acidChEBI
Acide cerebroniqueChEBI
CerebronsaeureChEBI
2-HydroxylignocerateGenerator
2-HydroxytetraeicosanoateGenerator
2-HydroxytetraicosanoateGenerator
CerebronateGenerator
a-Hydroxylignoceric acidHMDB
D-Cerebronic acidHMDB
Phrenosic acidHMDB
Phrenosinic acidHMDB
DL-CerebronateGenerator
Cerebronic acidMeSH
Chemical FormulaC24H48O3
Average Molecular Weight384.6361
Monoisotopic Molecular Weight384.360345402
IUPAC Name2-hydroxytetracosanoic acid
Traditional Namecerebronic acid
CAS Registry Number544-57-0
SMILES
CCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C24H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(25)24(26)27/h23,25H,2-22H2,1H3,(H,26,27)
InChI KeyMSUOLNSQHLHDAS-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
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.6e-05 g/LALOGPS
logP9.03ALOGPS
logP8.94ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity115.38 m³·mol⁻¹ChemAxon
Polarizability52.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8985000000-f869fb90b156d12a5b7fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9660460000-f1067f6f2156e5d9123aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-5d425cf531620d2182b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n1-2239000000-ce7f1c57bd637cb2f855Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-5892000000-9999feb10766cc7232d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-dd3507052099f2b71995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0009000000-b7c78e012a243ff79ec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adu-9108000000-bdff72b557a8c70fe17cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019157
KNApSAcK IDC00035013
Chemspider ID92507
KEGG Compound IDC17873
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102430
PDB IDNot Available
ChEBI ID61302
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.