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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002345
Secondary Accession Numbers
  • HMDB02345
Metabolite Identification
Common NameHeneicosanoic acid
DescriptionHenicosanoic acid, also known as N-heneicosanoate or 21:0,is a long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a henicosanoate. Heneicosanoic acid 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. Heneicosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heneicosanoic acid is a potentially toxic compound.
Structure
Data?1601278601
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 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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 76 °CNot Available
Boiling Point384.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00019 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.810 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+187.95931661259
DarkChem[M-H]-189.01431661259
DeepCCS[M+H]+184.88730932474
DeepCCS[M-H]-180.86830932474
DeepCCS[M-2H]-218.10330932474
DeepCCS[M+Na]+194.00730932474
AllCCS[M+H]+197.632859911
AllCCS[M+H-H2O]+195.032859911
AllCCS[M+NH4]+200.032859911
AllCCS[M+Na]+200.732859911
AllCCS[M-H]-189.432859911
AllCCS[M+Na-2H]-191.132859911
AllCCS[M+HCOO]-193.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heneicosanoic acidCCCCCCCCCCCCCCCCCCCCC(O)=O3499.7Standard polar33892256
Heneicosanoic acidCCCCCCCCCCCCCCCCCCCCC(O)=O2408.4Standard non polar33892256
Heneicosanoic acidCCCCCCCCCCCCCCCCCCCCC(O)=O2467.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heneicosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2539.2Semi standard non polar33892256
Heneicosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2795.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Heneicosanoic acid GC-MS (1 TMS)splash10-0159-2900000000-d29fc7eb4fea54b3bffe2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heneicosanoic acid GC-MS (Non-derivatized)splash10-0159-2900000000-d29fc7eb4fea54b3bffe2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9680000000-c0721d1f1430583b0cfe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9551000000-56b944394c02259484e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heneicosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05dl-9201000000-365f2ad065e0036dda862014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004i-0009000000-76ddc619babd8e5695ce2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-004i-0009000000-673b532d7cf4b18b12a92012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-001i-0090000000-c40174e878425a9d05072012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 40V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 40V, Negative-QTOFsplash10-004i-0009000000-de3d68bcc91dd21e1b822017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0009000000-b460efbbb047c9d921a02017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0009000000-50c83801cda9cc6185622017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0009000000-692538bbbc86d3d2a0082017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid Linear Ion Trap , negative-QTOFsplash10-001i-0912000000-73d16aa01cbd339c9d922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0009000000-de3d68bcc91dd21e1b822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0009000000-b460efbbb047c9d921a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0009000000-50c83801cda9cc6185622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0009000000-692538bbbc86d3d2a0082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid Linear Ion Trap , positive-QTOFsplash10-0973-0691000000-216228016fee98acf8692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid 30V, Positive-QTOFsplash10-004i-0009000000-400faab343cdd1639a7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Heneicosanoic acid 40V, Positive-QTOFsplash10-004i-0009000000-de3d68bcc91dd21e1b822021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 10V, Positive-QTOFsplash10-0a4i-0029000000-8ed29c4b9b431c1b25512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 20V, Positive-QTOFsplash10-0arr-2493000000-28f328152d5c637404712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 40V, Positive-QTOFsplash10-05mo-6970000000-ea3835b108a78f89fab72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 10V, Negative-QTOFsplash10-004i-0019000000-7ddcca4730bc179bc0c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 20V, Negative-QTOFsplash10-057i-1039000000-18ffc404f0bfd0d609212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heneicosanoic acid 40V, Negative-QTOFsplash10-0a4l-9130000000-d9a208c7e92c239a22b42017-09-01Wishart 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 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
FooDB IDFDB002742
KNApSAcK IDC00053301
Chemspider ID16012
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeneicosylic acid
METLIN ID4208
PubChem Compound16898
PDB IDNot Available
ChEBI ID39248
Food Biomarker OntologyNot Available
VMH IDM02053
MarkerDB IDNot Available
Good Scents IDrw1249221
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 ]