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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:33:23 UTC
HMDB IDHMDB0001160
Secondary Accession Numbers
  • HMDB01160
Metabolite Identification
Common NameTricosanoic acid
DescriptionTricosanoic acid, also known as N-tricosanoate or 22FA, 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. Tricosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tricosanoic acid is a potentially toxic compound.
Structure
Data?1582752180
Synonyms
ValueSource
N-Tricosanoic acidChEBI
N-TricosanoateGenerator
TricosanoateGenerator
22FAHMDB
F23HMDB
Tricosanoic acid, aluminum saltMeSH, HMDB
Tricosanoic acid, calcium saltMeSH, HMDB
Tricosanoic acid, lead saltMeSH, HMDB
TricosylateGenerator, HMDB
Tricosanoic acidMeSH
23FAPhytoBank
Tricosylic acidPhytoBank
FA(23:0)PhytoBank
Chemical FormulaC23H46O2
Average Molecular Weight354.6101
Monoisotopic Molecular Weight354.349780716
IUPAC Nametricosanoic acid
Traditional Nametricosanoic acid
CAS Registry Number2433-96-7
SMILES
CCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C23H46O2/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/h2-22H2,1H3,(H,24,25)
InChI KeyXEZVDURJDFGERA-UHFFFAOYSA-N
Chemical Taxonomy
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point77.0 - 79.0 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available196.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00002152
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.6e-05 g/LALOGPS
logP10(9.39) g/LALOGPS
logP10(9.37) g/LChemAxon
logS10(-7.1) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity109.29 m³·mol⁻¹ChemAxon
Polarizability49.4 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]+196.52831661259
DarkChem[M-H]-195.90131661259
AllCCS[M+H]+207.61832859911
AllCCS[M-H]-195.79132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tricosanoic acidCCCCCCCCCCCCCCCCCCCCCCC(O)=O3760.9Standard polar33892256
Tricosanoic acidCCCCCCCCCCCCCCCCCCCCCCC(O)=O2603.6Standard non polar33892256
Tricosanoic acidCCCCCCCCCCCCCCCCCCCCCCC(O)=O2664.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tricosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2738.2Semi standard non polar33892256
Tricosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2994.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tricosanoic acid GC-MS (1 TMS)splash10-0159-2900000000-90925cf3c5c344889a872014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tricosanoic acid GC-MS (Non-derivatized)splash10-0159-2900000000-90925cf3c5c344889a872017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8790000000-189d993955590b247b042017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9541000000-22eb85c1b6ca5b727ec22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tricosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0596-9201000000-4c4b474aedf9d85a53e12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0pvr-0298000000-80b9daf5924525f32b702012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-3390000000-ac935102623d865e251d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00l6-4980000000-ff160222688e5c3a5eba2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 40V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF , Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 40V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF , Negative-QTOFsplash10-014i-0090000000-1e57778151b8b2a053622017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 40V, Negative-QTOFsplash10-05fr-0590000000-455d8ab1313a61d90f8c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-0udi-0009000000-6cab4a327eae32b5f7872017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-0udi-0029000000-37d069e8e40dc21260552017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-0udi-0009000000-32d4687abf7d5b4744722017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid ESI-TOF , Negative-QTOFsplash10-0udi-0009000000-0756d3aa19109128f0752017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tricosanoic acid LC-ESI-TOF , negative-QTOFsplash10-05fr-0590000000-455d8ab1313a61d90f8c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 10V, Positive-QTOFsplash10-0a4r-0019000000-f057f22a9f1ae508491f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 20V, Positive-QTOFsplash10-0a4i-4698000000-93353ef0bd573ddf38562017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 40V, Positive-QTOFsplash10-0007-5890000000-a4664c743314ab26742e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 10V, Negative-QTOFsplash10-0udi-0009000000-e7720ae2787f40cc1c412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 20V, Negative-QTOFsplash10-0zfr-1009000000-972e00d6c61341c05ce82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tricosanoic acid 40V, Negative-QTOFsplash10-0a4i-9122000000-1a4a94c95b1a241675842017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2021-10-10Wishart LabView Spectrum
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 Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.033 +/- 0.004 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03500
Phenol Explorer Compound IDNot Available
FooDB IDFDB002894
KNApSAcK IDC00053866
Chemspider ID16170
KEGG Compound IDNot Available
BioCyc IDCPD-7834
BiGG IDNot Available
Wikipedia LinkTricosylic acid
METLIN ID4211
PubChem Compound17085
PDB IDNot Available
ChEBI ID42394
Food Biomarker OntologyNot Available
VMH IDM03045
MarkerDB IDNot Available
Good Scents IDrw1292281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. http://www.patentstorm.us/patents/4874791-description.html [Link]
  2. http://www.rain-tree.com/peppertree.htm [Link]