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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2019-01-11 19:16:58 UTC
HMDB IDHMDB0002345
Secondary Accession Numbers
  • HMDB02345
Metabolite Identification
Common NameHeneicosanoic acid
DescriptionHeneicosanoic acid (HEA) is a fatty acid found in human milk fat (PMID: 16332663 , 16512938 ). HEA is also a part of the phospholipids of the articular cartilage boundary lubricant (PMID: 11518278 ). HEA is a constituent of red blood cell fatty acids. (PMID: 9972864 ).
Structure
Data?1547234218
Synonyms
ValueSource
21:0ChEBI
C21:0ChEBI
HeneicosansaeureChEBI
Heneicosylic acidChEBI
N-Heneicosanoic acidChEBI
N-Heneicosylic acidChEBI
N-Henicosanoic acidChEBI
HeneicosylateGenerator
N-HeneicosanoateGenerator
N-HeneicosylateGenerator
N-HenicosanoateGenerator
HeneicosanoateGenerator
HeneicosanateHMDB
Heneicosanic acidHMDB
HenicosanoateHMDB
Henicosanoic acidHMDB
Heneicosanoic acidChEBI
Chemical FormulaC21H42O2
Average Molecular Weight326.557
Monoisotopic Molecular Weight326.318480588
IUPAC Namehenicosanoic acid
Traditional Nameheneicosanoic acid
CAS Registry Number2363-71-5
SMILES
CCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C21H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23/h2-20H2,1H3,(H,22,23)
InChI KeyCKDDRHZIAZRDBW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • 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 Point74 - 76 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.0e-05 g/LALOGPS
logP8.97ALOGPS
logP8.48ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity100.09 m³·mol⁻¹ChemAxon
Polarizability45.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-d29fc7eb4fea54b3bffeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-d29fc7eb4fea54b3bffeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9680000000-c0721d1f1430583b0cfeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9551000000-56b944394c02259484e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0009000000-76ddc619babd8e5695ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-0009000000-673b532d7cf4b18b12a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0090000000-c40174e878425a9d0507JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0009000000-b460efbbb047c9d921a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-50c83801cda9cc618562JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0009000000-692538bbbc86d3d2a008JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0912000000-73d16aa01cbd339c9d92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-b460efbbb047c9d921a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-50c83801cda9cc618562JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-692538bbbc86d3d2a008JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0973-0691000000-216228016fee98acf869JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0029000000-8ed29c4b9b431c1b2551JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-2493000000-28f328152d5c63740471JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-6970000000-ea3835b108a78f89fab7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-7ddcca4730bc179bc0c2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1039000000-18ffc404f0bfd0d60921JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-d9a208c7e92c239a22b4JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-05dl-9201000000-365f2ad065e0036dda86JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
FoodDB IDFDB002742
KNApSAcK IDNot Available
Chemspider ID16012
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeneicosylic acid
METLIN ID4208
PubChem Compound16898
PDB IDNot Available
ChEBI ID39248
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Moser AB, Jones DS, Raymond GV, Moser HW: Plasma and red blood cell fatty acids in peroxisomal disorders. Neurochem Res. 1999 Feb;24(2):187-97. [PubMed:9972864 ]
  2. Mosley EE, Wright AL, McGuire MK, McGuire MA: trans Fatty acids in milk produced by women in the United States. Am J Clin Nutr. 2005 Dec;82(6):1292-7. [PubMed:16332663 ]
  3. Torres AG, Ney JG, Meneses F, Trugo NM: Polyunsaturated fatty acids and conjugated linoleic acid isomers in breast milk are associated with plasma non-esterified and erythrocyte membrane fatty acid composition in lactating women. Br J Nutr. 2006 Mar;95(3):517-24. [PubMed:16512938 ]
  4. Sarma AV, Powell GL, LaBerge M: Phospholipid composition of articular cartilage boundary lubricant. J Orthop Res. 2001 Jul;19(4):671-6. [PubMed:11518278 ]