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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2021-10-13 04:39:03 UTC
HMDB IDHMDB0002361
Secondary Accession Numbers
  • HMDB02361
Metabolite Identification
Common NamePentacosanoic acid
DescriptionPentacosanoic acid, also known as pentacosanoate or hyenate, is a straight-chain saturated fatty acid and a very long-chain fatty acid. It is a conjugate acid of a pentacosanoate. Pentacosanoic acid 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. Pentacosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Pentacosanoic acid is a potentially toxic compound.
Structure
Data?1582752245
Synonyms
ValueSource
PentacosanoateGenerator
HyenateHMDB, Generator
Hyenic acidHMDB
N-PentacosanoateHMDB
N-Pentacosanoic acidHMDB
Chemical FormulaC25H50O2
Average Molecular Weight382.6633
Monoisotopic Molecular Weight382.381080844
IUPAC Namepentacosanoic acid
Traditional Namepentacosanoic acid
CAS Registry Number506-38-7
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C25H50O2/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/h2-24H2,1H3,(H,26,27)
InChI KeyMWMPEAHGUXCSMY-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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP10(9.73) g/LALOGPS
logP10(10.26) g/LChemAxon
logS10(-7.3) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity118.49 m³·mol⁻¹ChemAxon
Polarizability53.74 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]+203.57631661259
DarkChem[M-H]-204.34531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pentacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O4024.1Standard polar33892256
Pentacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O2803.1Standard non polar33892256
Pentacosanoic acidCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O2865.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pentacosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2935.3Semi standard non polar33892256
Pentacosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3193.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pentacosanoic acid GC-MS (1 TMS)splash10-0159-2900000000-6665b7d9eabf93c4a9452014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentacosanoic acid GC-MS (Non-derivatized)splash10-0159-2900000000-6665b7d9eabf93c4a9452017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-8890000000-725d043b2157b24da3a42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9550000000-96d63a4885fdd05441652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentacosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pentacosanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0009000000-800d2e5558f9293777f22012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 10V, Positive-QTOFsplash10-014i-0009000000-f070114e9b2a4bbf66792017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 20V, Positive-QTOFsplash10-00yr-3339000000-b176744191f8a42e707b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 40V, Positive-QTOFsplash10-006x-5972000000-b415c1ccaa8f4d57a5292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 10V, Negative-QTOFsplash10-001i-0009000000-8dfc981003ca4996a4892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 20V, Negative-QTOFsplash10-01qi-0009000000-ef611c789ccafd81219e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 40V, Negative-QTOFsplash10-0a4l-9113000000-8f4bec5516a7678910612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 10V, Negative-QTOFsplash10-001i-0009000000-df18d224d3bce420cd792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 20V, Negative-QTOFsplash10-01q9-1009000000-397f2820fbfdd63fd68f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 40V, Negative-QTOFsplash10-0006-9012000000-d56100016e8ed9e82fc12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 10V, Positive-QTOFsplash10-00lr-2009000000-8d7bf9f66523c92f4b8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 20V, Positive-QTOFsplash10-066r-8049000000-b0deb3a758569827538a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentacosanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-c5daab40fd34bd3117842021-09-22Wishart 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 Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003081
KNApSAcK IDC00057417
Chemspider ID10036
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentacosylic acid
METLIN ID4209
PubChem Compound10468
PDB IDNot Available
ChEBI ID39420
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1824601
References
Synthesis ReferenceCason, James; Wolfhagen, Helen J.; Tarpey, Winifred; Adams, Raylene E. Branched chain fatty acids. X. Synthesis of acids with branching methyl groups near the carboxyl. Journal of Organic Chemistry (1949), 14 147-54.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Reinecke CJ, Knoll DP, Pretorius PJ, Steyn HS, Simpson RH: The correlation between biochemical and histopathological findings in adrenoleukodystrophy. J Neurol Sci. 1985 Aug;70(1):21-38. [PubMed:4045498 ]
  2. Tao RV, Lee BC, Hsieh TC, Laine RA: Occurrence of an unusual amount of an odd-numbered fatty acid in glycosphingolipids from human cataracts. Curr Eye Res. 1987 Dec;6(12):1361-7. [PubMed:3427985 ]