You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2018-05-20 00:27:02 UTC
HMDB IDHMDB0002361
Secondary Accession Numbers
  • HMDB02361
Metabolite Identification
Common NamePentacosanoic acid
DescriptionHyenic acid, also known as hyenate or N-pentacosanoate, 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. Hyenic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Hyenic acid has been detected in multiple biofluids, such as feces and urine. Within the cell, hyenic acid is primarily located in the membrane (predicted from logP), cytoplasm and adiposome. Hyenic acid is also a parent compound for other transformation products, including but not limited to, 24-methylpentacosanoic acid, N-pentacosanoyl-14-methylhexadecasphingosine-1-phosphocholine, and 2-hydroxypentacosanoic acid. Outside of the human body, hyenic acid can be found in citrus. This makes hyenic acid a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
HyenateHMDB
Hyenic acidHMDB
N-PentacosanoateHMDB
N-Pentacosanoic acidHMDB
PentacosanoateHMDB
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
DescriptionThis compound 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 Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP9.73ALOGPS
logP10.26ChemAxon
logS-7.3ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-6665b7d9eabf93c4a945View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-6665b7d9eabf93c4a945View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-8890000000-725d043b2157b24da3a4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9550000000-96d63a4885fdd0544165View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-800d2e5558f9293777f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-f070114e9b2a4bbf6679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yr-3339000000-b176744191f8a42e707bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-5972000000-b415c1ccaa8f4d57a529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-8dfc981003ca4996a489View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0009000000-ef611c789ccafd81219eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-8f4bec5516a767891061View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Infant (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
FoodDB IDFDB003081
KNApSAcK IDNot Available
Chemspider ID10036
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentacosylic acid
METLIN ID4209
PubChem Compound10468
PDB IDNot Available
ChEBI ID39420
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 ]