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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:01:39 UTC
Update Date2022-09-22 18:34:27 UTC
HMDB IDHMDB0039540
Secondary Accession Numbers
  • HMDB39540
Metabolite Identification
Common NameCerebronic acid
DescriptionCerebronic acid, also known as cerebronsaeure, 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. Based on a literature review a significant number of articles have been published on Cerebronic acid.
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.49131661259
DarkChem[M-H]-203.11531661259
DeepCCS[M+H]+198.14430932474
DeepCCS[M-H]-195.20530932474
DeepCCS[M-2H]-229.8930932474
DeepCCS[M+Na]+206.1830932474
AllCCS[M+H]+216.932859911
AllCCS[M+H-H2O]+214.732859911
AllCCS[M+NH4]+219.032859911
AllCCS[M+Na]+219.532859911
AllCCS[M-H]-200.232859911
AllCCS[M+Na-2H]-202.232859911
AllCCS[M+HCOO]-204.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cerebronic acidCCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O4089.9Standard polar33892256
Cerebronic acidCCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O2769.6Standard non polar33892256
Cerebronic acidCCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O2919.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cerebronic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O2971.8Semi standard non polar33892256
Cerebronic acid,1TMS,isomer #2CCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C2986.5Semi standard non polar33892256
Cerebronic acid,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C3003.4Semi standard non polar33892256
Cerebronic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O3254.9Semi standard non polar33892256
Cerebronic acid,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C(C)(C)C3233.6Semi standard non polar33892256
Cerebronic acid,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3512.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cerebronic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8985000000-f869fb90b156d12a5b7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cerebronic acid GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9660460000-f1067f6f2156e5d9123a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cerebronic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 10V, Positive-QTOFsplash10-000i-0009000000-5d425cf531620d2182b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 20V, Positive-QTOFsplash10-05n1-2239000000-ce7f1c57bd637cb2f8552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 40V, Positive-QTOFsplash10-052f-5892000000-9999feb10766cc7232d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 10V, Negative-QTOFsplash10-001i-0009000000-dd3507052099f2b719952016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 20V, Negative-QTOFsplash10-0019-0009000000-b7c78e012a243ff79ec32016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 40V, Negative-QTOFsplash10-0adu-9108000000-bdff72b557a8c70fe17c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 10V, Negative-QTOFsplash10-001i-0009000000-e54470fa4297f77753552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 20V, Negative-QTOFsplash10-001i-1009000000-c12ef71f796c05aab17b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 40V, Negative-QTOFsplash10-0006-9000000000-b4cddce7ddf032651e002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 10V, Positive-QTOFsplash10-000i-2009000000-f770eee571295521bce92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 20V, Positive-QTOFsplash10-05n0-7159000000-0e17c2756dd2f3e53fab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cerebronic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-9fc74b6abb9c06bf81da2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019156
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
MarkerDB IDNot Available
Good Scents IDrw1878201
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.