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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2022-03-07 02:49:12 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
Data?1582752226
Synonyms
ValueSource
C27:0ChEBI
Carboceric acidChEBI
CarbocerateGenerator
HeptacosanoateGenerator
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
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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+212.01731661259
DarkChem[M-H]-213.00831661259
DeepCCS[M+H]+203.63330932474
DeepCCS[M-H]-201.08330932474
DeepCCS[M-2H]-234.43230932474
DeepCCS[M+Na]+209.97630932474
AllCCS[M+H]+226.432859911
AllCCS[M+H-H2O]+224.432859911
AllCCS[M+NH4]+228.232859911
AllCCS[M+Na]+228.732859911
AllCCS[M-H]-208.032859911
AllCCS[M+Na-2H]-210.832859911
AllCCS[M+HCOO]-213.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heptacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O4276.4Standard polar33892256
Heptacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O2998.7Standard non polar33892256
Heptacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O3065.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heptacosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C3131.3Semi standard non polar33892256
Heptacosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3394.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Heptacosanoic acid GC-MS (1 TMS)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heptacosanoic acid GC-MS (Non-derivatized)splash10-0159-3900000000-0d5ed9b39f3c76ee5fc42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptacosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8890000000-7396516eb442152dbb022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptacosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9550000000-c0d8e10f26ee0e7558a22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptacosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptacosanoic 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 - Heptacosanoic acid 10V, Positive-QTOFsplash10-03dl-0009700000-838438b927ed484928e12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 20V, Positive-QTOFsplash10-0i03-3439100000-b5876a9e8006b51ac77b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 40V, Positive-QTOFsplash10-0f6x-5962000000-eb27d6556c6334d60cdc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 10V, Negative-QTOFsplash10-0a4i-0002900000-6fc37d2544da8b02c0dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 20V, Negative-QTOFsplash10-0a4i-1007900000-8e281e17ea1c3bb6fe1b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 40V, Negative-QTOFsplash10-0a4l-9113000000-2d6057b8ac87b85ad1562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 10V, Negative-QTOFsplash10-0a4i-0001900000-14c99062a351c820c5ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 20V, Negative-QTOFsplash10-0a4l-1005900000-da34a90fa8dfc4f625622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 40V, Negative-QTOFsplash10-0006-9002000000-7bc0e269fa202e5bccbb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 10V, Positive-QTOFsplash10-03dl-4019700000-0111d4e138997735fab22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 20V, Positive-QTOFsplash10-052f-8039200000-e925ebdca83ee37d69872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptacosanoic acid 40V, Positive-QTOFsplash10-0a4l-9010000000-8226506239927e4142482021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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
FooDB IDFDB022826
KNApSAcK IDC00053305
Chemspider ID21994
KEGG Compound IDNot Available
BioCyc IDCPD-7829
BiGG IDNot Available
Wikipedia LinkCarboceric acid
METLIN ID6466
PubChem Compound23524
PDB IDNot Available
ChEBI ID78710
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]