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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2017-10-23 19:03:59 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
Thumb
Synonyms
ValueSource
21:0ChEBI
C21:0ChEBI
HeneicosansaeureChEBI
Heneicosylic acidChEBI
N-Heneicosanoic acidChEBI
N-Heneicosylic acidChEBI
N-Henicosanoic acidChEBI
HeneicosanoateGenerator
HeneicosylateGenerator
N-HeneicosanoateGenerator
N-HeneicosylateGenerator
N-HenicosanoateGenerator
HeneicosanateHMDB
Heneicosanic acidHMDB
HenicosanoateHMDB
Henicosanoic acidHMDB
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
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Indirect biological 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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-d29fc7eb4fea54b3bffeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-d29fc7eb4fea54b3bffeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9680000000-c0721d1f1430583b0cfeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9551000000-56b944394c02259484e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0009000000-76ddc619babd8e5695ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-0009000000-673b532d7cf4b18b12a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0090000000-c40174e878425a9d0507View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0009000000-b460efbbb047c9d921a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-50c83801cda9cc618562View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0009000000-692538bbbc86d3d2a008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0912000000-73d16aa01cbd339c9d92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-b460efbbb047c9d921a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-50c83801cda9cc618562View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-692538bbbc86d3d2a008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0973-0691000000-216228016fee98acf869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0029000000-8ed29c4b9b431c1b2551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-2493000000-28f328152d5c63740471View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-6970000000-ea3835b108a78f89fab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-7ddcca4730bc179bc0c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1039000000-18ffc404f0bfd0d60921View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-d9a208c7e92c239a22b4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05dl-9201000000-365f2ad065e0036dda86View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002742
KNApSAcK IDNot Available
Chemspider ID16012
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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 ]