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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2021-09-07 16:45:33 UTC
HMDB IDHMDB0002348
Secondary Accession Numbers
  • HMDB02348
Metabolite Identification
Common NameOctacosanoic acid
DescriptionOctacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID:2474624 ). Octacosanoic acid is a higher aliphatic primary acids purified from sugar-cane (Saccharum officinarum L.) wax that has been shown to inhibit platelet aggregation induced ex vivo by addition of agonists to platelet-rich plasma (PRP) of rats, guinea pigs, and healthy human volunteers. (PMID:5099499 ). Octacosanoic acid is formed from octacosanol via beta-oxidation. (PMID:15847942 ).
Structure
Data?1582752244
Synonyms
ValueSource
1-Octacosanoic acidChEBI
CH3-[CH2]26-COOHChEBI
Montanic acidChEBI
N-Octacosanoic acidChEBI
N-Octaeicosanoic acidChEBI
OctacosancarbonsaeureChEBI
OctacosansaeureChEBI
Octacosoic acidChEBI
Octaeicosanoic acidChEBI
1-OctacosanoateGenerator
MontanateGenerator
N-OctacosanoateGenerator
N-OctaeicosanoateGenerator
OctacosoateGenerator
OctaeicosanoateGenerator
OctacosanoateGenerator
Octacosanoic acid, 1-2 calcium saltMeSH, HMDB
Octacosanoic acidMeSH
Chemical FormulaC28H56O2
Average Molecular Weight424.743
Monoisotopic Molecular Weight424.428031036
IUPAC Nameoctacosanoic acid
Traditional Nameoctacosanoic acid
CAS Registry Number506-48-9
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C28H56O2/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)30/h2-27H2,1H3,(H,29,30)
InChI KeyUTOPWMOLSKOLTQ-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.5e-05 g/LALOGPS
logP10.11ALOGPS
logP11.59ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity132.3 m³·mol⁻¹ChemAxon
Polarizability60.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available215.77231661259
DarkChem[M-H]-PredictedNot Available215.81831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Octacosanoic acid,1TMS,#13229.1184https://arxiv.org/abs/1905.12712
Octacosanoic acid,1TBDMS,#13494.731https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-015a-1900000000-58c72f07b64a0561338d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-3900100000-34225aef9330c47437c02014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-015a-1900000000-58c72f07b64a0561338d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-3900100000-34225aef9330c47437c02017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7970000000-c94a43bb5bc46c5071cc2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-1dbd0ba0052b40b0cb0c2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-05fu-9200100000-a1e6c74a1e455906fd842014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0020900000-38ac2a13b58f10f626f72012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002b-0942700000-00dc2499f3a7191748fb2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00r2-8900000000-a826aa016c3aee7f31642012-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-5053554af4cc5fc398352017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-3449400000-423526b92fd641c6bf0f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-7974000000-400dfc77ba97ac62ae002017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-aaf485cd3e6ba25073192017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-1003900000-b15c91e2c70889b2f2092017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-2b4dc4a33e559f5501312017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-3002900000-b5c62f7b0c138068c4ba2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9027600000-dda5ed1ff49b80af804a2021-09-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-2badc125175359e5b85b2021-09-21View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
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 IDFDB007128
KNApSAcK IDC00051638
Chemspider ID10038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMontanic_acid
METLIN ID6638
PubChem Compound10470
PDB IDNot Available
ChEBI ID31001
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Menendez R, Marrero D, Mas R, Fernandez I, Gonzalez L, Gonzalez RM: In vitro and in vivo study of octacosanol metabolism. Arch Med Res. 2005 Mar-Apr;36(2):113-9. [PubMed:15847942 ]
  2. 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 ]
  3. Lankin VZ, Sadovnikova IP: [Simple quantitative method of direct transesterification of higher fatty acid in biological samples]. Vopr Med Khim. 1971 May-Jun;17(3):331-5. [PubMed:5099499 ]