Heneicosanoic acid (CHEM003573)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-05 17:14:00 UTC
Update Date2026-04-17 16:09:11 UTC
Accession NumberCHEM003573
Identification
Common NameHeneicosanoic acid
ClassSmall Molecule
DescriptionHeneicosanoic acid (HEA) is a fatty acid found in human milk fat (1, 2). HEA is also a part of the phospholipids of the articular cartilage boundary lubricant (3). HEA is a constituent of red blood cell fatty acids. (4).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
FA(21:0)PhytoBank
Chemical FormulaC21H42O2
Average Molecular Mass326.557 g/mol
Monoisotopic Mass326.318 g/mol
CAS Registry Number2363-71-5
IUPAC Namehenicosanoic acid
Traditional Nameheneicosanoic acid
SMILESCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point74 - 76 °C
Boiling PointNot Available
SolubilityNot 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-d29fc7eb4fea54b3bffeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-d29fc7eb4fea54b3bffeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9680000000-c0721d1f1430583b0cfeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9551000000-56b944394c02259484e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0009000000-76ddc619babd8e5695ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-0009000000-673b532d7cf4b18b12a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0090000000-c40174e878425a9d0507Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0009000000-b460efbbb047c9d921a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-50c83801cda9cc618562Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0009000000-692538bbbc86d3d2a008Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0912000000-73d16aa01cbd339c9d92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-de3d68bcc91dd21e1b82Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-b460efbbb047c9d921a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-50c83801cda9cc618562Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-692538bbbc86d3d2a008Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0973-0691000000-216228016fee98acf869Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0009000000-400faab343cdd1639a7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0009000000-de3d68bcc91dd21e1b82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0029000000-8ed29c4b9b431c1b2551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0arr-2493000000-28f328152d5c63740471Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-6970000000-ea3835b108a78f89fab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-7ddcca4730bc179bc0c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1039000000-18ffc404f0bfd0d60921Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-d9a208c7e92c239a22b4Spectrum
MSMass Spectrum (Electron Ionization)splash10-05dl-9201000000-365f2ad065e0036dda86Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002345
FooDB IDFDB002742
Phenol Explorer IDNot Available
KNApSAcK IDC00053301
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID4208
PDB IDNot Available
Wikipedia LinkHeneicosylic acid
Chemspider ID16012
ChEBI ID39248
PubChem Compound ID16898
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16332663
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9965255
3. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
4. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
5. 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.
6. 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.
7. Sarma AV, Powell GL, LaBerge M: Phospholipid composition of articular cartilage boundary lubricant. J Orthop Res. 2001 Jul;19(4):671-6.
8. 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.