Heptacosanoic acid (CHEM003569)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-05 17:13:31 UTC
Update Date2026-04-04 19:26:52 UTC
Accession NumberCHEM003569
Identification
Common NameHeptacosanoic acid
ClassSmall Molecule
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. (1). 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). (2). Heptacosanoic acid has been found in the adrenal cortex and brain, in adrenoleukodystrophy and Zellweger syndrome in humans. (3). 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). (4).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C27:0ChEBI
Carboceric acidChEBI
CarbocerateGenerator
HeptacosanoateGenerator
Chemical FormulaC27H54O2
Average Molecular Mass410.717 g/mol
Monoisotopic Mass410.412 g/mol
CAS Registry Number7138-40-1
IUPAC NameNot Available
Traditional Nameheptacosanoic acid
SMILESCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8890000000-7396516eb442152dbb02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9550000000-c0d8e10f26ee0e7558a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009700000-838438b927ed484928e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-3439100000-b5876a9e8006b51ac77bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-5962000000-eb27d6556c6334d60cdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-6fc37d2544da8b02c0ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1007900000-8e281e17ea1c3bb6fe1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-2d6057b8ac87b85ad156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-14c99062a351c820c5edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1005900000-da34a90fa8dfc4f62562Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9002000000-7bc0e269fa202e5bccbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-4019700000-0111d4e138997735fab2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-8039200000-e925ebdca83ee37d6987Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-8226506239927e414248Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002063
FooDB IDFDB022826
Phenol Explorer IDNot Available
KNApSAcK IDC00053305
BiGG IDNot Available
BioCyc IDCPD-7829
METLIN ID6466
PDB IDNot Available
Wikipedia LinkCarboceric acid
Chemspider ID21994
ChEBI ID78710
PubChem Compound ID23524
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24746767
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7276981
3. 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.
4. 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.
5. 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.
6. 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.