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Showing metabocard for Heptacosanoic acid (HMDB0002063)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-12-07 01:46:59 UTC
HMDB IDHMDB0002063
Secondary Accession Numbers
  • HMDB02063
Metabolite Identification
Common NameHeptacosanoic acid
DescriptionHeptacosanoic acid is a fatty acid found in follicular casts (the abnormal impactation of a sebaceous follicle) implicated as the preclinical lesion of acne vulgaris. (PMID: 2940302 ). Heptacosanoic acid is one of the fatty acids found that contribute to a significant increase in the microviscosity of erythrocyte membranes in patients affected with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). (PMID: 6874949 ). Heptacosanoic acid has been found in the adrenal cortex and brain, in adrenoleukodystrophy and Zellweger syndrome in humans. (PMID: 3806133 ). Heptacosanoic acid has been found in blood and tissues of patients with different genetic peroxisomal disorder (Refsum's disease, X-linked adrenoleukodystrophy, neonatal adrenoleukodystrophy or Zellweger syndrome). (PMID: 2474624 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C27:0ChEBI
Carboceric acidChEBI
HeptacosanoateGenerator
CarbocerateGenerator
Chemical FormulaC27H54O2
Average Molecular Weight410.7165
Monoisotopic Molecular Weight410.412380972
IUPAC Nameheptacosanoic acid
Traditional Nameheptacosanoic acid
CAS Registry Number7138-40-1
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C27H54O2/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)29/h2-26H2,1H3,(H,28,29)
InChI KeyVXZBFBRLRNDJCS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
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 Solubility1.7e-05 g/LALOGPS
logP9.98ALOGPS
logP11.15ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity127.69 m³·mol⁻¹ChemAxon
Polarizability58.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8890000000-7396516eb442152dbb02View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9550000000-c0d8e10f26ee0e7558a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009700000-838438b927ed484928e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-3439100000-b5876a9e8006b51ac77bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-5962000000-eb27d6556c6334d60cdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-6fc37d2544da8b02c0ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1007900000-8e281e17ea1c3bb6fe1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-2d6057b8ac87b85ad156View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationNot 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 IDFDB022826
KNApSAcK IDNot Available
Chemspider ID21994
KEGG Compound IDNot Available
BioCyc IDCPD-7829
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6466
PubChem Compound23524
PDB IDNot Available
ChEBI ID78710
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Molzer B, Kainz-Korschinsky M, Sundt-Heller R, Bernheimer H: Phytanic acid and very long chain fatty acids in genetic peroxisomal disorders. J Clin Chem Clin Biochem. 1989 May;27(5):309-14. [PubMed:2474624 ]
  2. Nordstrom KM, Labows JN, McGinley KJ, Leyden JJ: Characterization of wax esters, triglycerides, and free fatty acids of follicular casts. J Invest Dermatol. 1986 Jun;86(6):700-5. [PubMed:2940302 ]
  3. Knazek RA, Rizzo WB, Schulman JD, Dave JR: Membrane microviscosity is increased in the erythrocytes of patients with adrenoleukodystrophy and adrenomyeloneuropathy. J Clin Invest. 1983 Jul;72(1):245-8. [PubMed:6874949 ]
  4. Yamamoto H, Yamamoto T, Konno H, Tezuka F, Iwasaki Y: Gas chromatography-electron impact-mass spectrometry (GC-EI-MS) analysis of saturated fatty acid compositions in formalin-fixed human tissues. J Neurol Sci. 1987 Jan;77(1):1-10. [PubMed:3806133 ]