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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2022-03-07 02:49:14 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.6e-08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+215.77231661259
DarkChem[M-H]-215.81831661259
DeepCCS[M+H]+206.99130932474
DeepCCS[M-H]-204.44130932474
DeepCCS[M-2H]-237.64330932474
DeepCCS[M+Na]+213.33430932474
AllCCS[M+H]+230.732859911
AllCCS[M+H-H2O]+228.932859911
AllCCS[M+NH4]+232.532859911
AllCCS[M+Na]+233.032859911
AllCCS[M-H]-211.232859911
AllCCS[M+Na-2H]-214.132859911
AllCCS[M+HCOO]-217.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Octacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O4401.1Standard polar33892256
Octacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O3092.5Standard non polar33892256
Octacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O3165.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octacosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C3229.1Semi standard non polar33892256
Octacosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3494.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Octacosanoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-015a-1900000000-58c72f07b64a0561338d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octacosanoic acid GC-MS (1 TMS)splash10-0159-3900100000-34225aef9330c47437c02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octacosanoic acid GC-EI-TOF (Non-derivatized)splash10-015a-1900000000-58c72f07b64a0561338d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octacosanoic acid GC-MS (Non-derivatized)splash10-0159-3900100000-34225aef9330c47437c02017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octacosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7970000000-c94a43bb5bc46c5071cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octacosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-1dbd0ba0052b40b0cb0c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octacosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05fu-9200100000-a1e6c74a1e455906fd842014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octacosanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-0020900000-38ac2a13b58f10f626f72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octacosanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-002b-0942700000-00dc2499f3a7191748fb2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octacosanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00r2-8900000000-a826aa016c3aee7f31642012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 10V, Positive-QTOFsplash10-0a6r-0002900000-5053554af4cc5fc398352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 20V, Positive-QTOFsplash10-05r0-3449400000-423526b92fd641c6bf0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 40V, Positive-QTOFsplash10-0296-7974000000-400dfc77ba97ac62ae002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 10V, Negative-QTOFsplash10-00di-0001900000-aaf485cd3e6ba25073192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 20V, Negative-QTOFsplash10-05i0-1003900000-b15c91e2c70889b2f2092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 40V, Negative-QTOFsplash10-0a4l-9113000000-2b4dc4a33e559f5501312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 10V, Positive-QTOFsplash10-056r-3002900000-b5c62f7b0c138068c4ba2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 20V, Positive-QTOFsplash10-0a4i-9027600000-dda5ed1ff49b80af804a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 40V, Positive-QTOFsplash10-0a4l-9010000000-2badc125175359e5b85b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 10V, Negative-QTOFsplash10-00di-0000900000-b9024a8d18f6acb5ce372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 20V, Negative-QTOFsplash10-05fr-1000900000-0508eeb1764771afaf8a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octacosanoic acid 40V, Negative-QTOFsplash10-0596-9001100000-51b30ca86b20536752de2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView 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
Good Scents IDrw1270381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. 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 ]
  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 ]