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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 09:59:38 UTC
HMDB IDHMDB0001160
Secondary Accession Numbers
  • HMDB01160
Metabolite Identification
Common NameTricosanoic acid
DescriptionTricosylic acid, also known as N-tricosanoate or tricosylate, 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. Tricosylic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Tricosylic acid has been detected in multiple biofluids, such as blood and urine. Within the cell, tricosylic acid is primarily located in the membrane (predicted from logP), cytoplasm and adiposome. Tricosylic acid is also a parent compound for other transformation products, including but not limited to, beta-D-galactosyl-N-(tricosanoyl)sphingosine, beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-N-tricosanoylsphingosine, and N-(tricosanoyl)-[(4E,6E)-tetradecasphingadienine]-1-phosphoethanolamine. Outside of the human body, tricosylic acid can be found in citrus, date, and papaya. This makes tricosylic acid a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
N-Tricosanoic acidChEBI
N-TricosanoateGenerator
TricosanoateGenerator
22FAHMDB
F23HMDB
Tricosanoic acid, aluminum saltMeSH
Tricosanoic acid, calcium saltMeSH
Tricosanoic acid, lead saltMeSH
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
DescriptionThis compound 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point77.0 - 79.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.6e-05 g/LALOGPS
logP9.39ALOGPS
logP9.37ChemAxon
logS-7.1ALOGPS
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
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)splash10-0159-2900000000-90925cf3c5c344889a87View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-90925cf3c5c344889a87View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8790000000-189d993955590b247b04View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9541000000-22eb85c1b6ca5b727ec2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pvr-0298000000-80b9daf5924525f32b70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3390000000-ac935102623d865e251dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00l6-4980000000-ff160222688e5c3a5ebaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-1e57778151b8b2a05362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-05fr-0590000000-455d8ab1313a61d90f8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-6cab4a327eae32b5f787View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0029000000-37d069e8e40dc2126055View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-32d4687abf7d5b474472View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-0756d3aa19109128f075View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-05fr-0590000000-455d8ab1313a61d90f8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0019000000-f057f22a9f1ae508491fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4698000000-93353ef0bd573ddf3856View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-5890000000-a4664c743314ab26742eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-e7720ae2787f40cc1c41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1009000000-972e00d6c61341c05ce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9122000000-1a4a94c95b1a24167584View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-9201000000-4c4b474aedf9d85a53e1View 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)
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 Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>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
FoodDB IDFDB002894
KNApSAcK IDNot Available
Chemspider ID16170
KEGG Compound IDNot Available
BioCyc IDCPD-7834
BiGG IDNot Available
Wikipedia LinkTricosylic acid
METLIN ID4211
PubChem Compound17085
PDB IDF23
ChEBI ID42394
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]