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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2021-10-13 04:36:56 UTC
HMDB IDHMDB0002003
Secondary Accession Numbers
  • HMDB02003
Metabolite Identification
Common NameTetracosanoic acid
DescriptionTetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, 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. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound.
Structure
Data?1582752222
Synonyms
ValueSource
CH3-[CH2]22-COOHChEBI
Lignoceric acidChEBI
LignozerinsaeureChEBI
N-Tetracosanoic acidChEBI
Tetracosanic acidChEBI
TetracosansaeureChEBI
Tetracosoic acidChEBI
Tetraeicosanoic acidChEBI
Tetraicosanoic acidChEBI
LignocerateGenerator
N-TetracosanoateGenerator
TetracosanateGenerator
TetracosoateGenerator
TetraeicosanoateGenerator
TetraicosanoateGenerator
TetracosanoateGenerator
Lignoceric acid, silver (1+) saltHMDB
Lignoceric acid, sodium saltHMDB
Lignoceric acid, potassium saltHMDB
Tetracosanoic acid, potassium salt (1:1)HMDB
Potassium tetracosanoateHMDB
Tetracosanoic acidMeSH
FA(24:0)PhytoBank
Chemical FormulaC24H48O2
Average Molecular Weight368.6367
Monoisotopic Molecular Weight368.36543078
IUPAC Nametetracosanoic acid
Traditional Namelignoceric acid
CAS Registry Number557-59-5
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C24H48O2/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)26/h2-23H2,1H3,(H,25,26)
InChI KeyQZZGJDVWLFXDLK-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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84.2 °CNot Available
Boiling Point405.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP11.400 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg197.93130932474
[M-H]-Not Available199.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000260
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP10(9.56) g/LALOGPS
logP10(9.81) g/LChemAxon
logS10(-7.2) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity113.89 m³·mol⁻¹ChemAxon
Polarizability51.57 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]+199.6431661259
DarkChem[M-H]-199.78631661259
DeepCCS[M+H]+194.37230932474
DeepCCS[M-H]-190.35230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetracosanoic acidCCCCCCCCCCCCCCCCCCCCCCCC(O)=O3893.2Standard polar33892256
Tetracosanoic acidCCCCCCCCCCCCCCCCCCCCCCCC(O)=O2703.4Standard non polar33892256
Tetracosanoic acidCCCCCCCCCCCCCCCCCCCCCCCC(O)=O2764.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetracosanoic acid,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2836.6Semi standard non polar33892256
Tetracosanoic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3094.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid GC-MS (1 TMS)splash10-0159-2900000000-9dedfb3583ae4e5539482014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid EI-B (Non-derivatized)splash10-07bf-9000000000-2ae141518702212751a72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid GC-MS (Non-derivatized)splash10-0159-2900000000-9dedfb3583ae4e5539482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetracosanoic acid GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-2826f8c66ba3647dda0f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-51ad38c3eba8f98c35652016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-6d38b4af18d7872e12a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetracosanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0avl-9200000000-6a6f857b59886189b2462014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-016r-0509000000-b590f3868a4aa3c868032012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-0903000000-a6d1b482b61c2d36ee1d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-0900000000-4ef3dd8c92115a6d4e0c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-07bf-9000000000-2ae141518702212751a72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0a4i-0900000000-3c3e69329be8a71480762012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-004r-0791000000-10ab351997f48e5126572017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 20V, Negative-QTOFsplash10-014i-0009000000-5c9df57aa4e8e48bd80f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-014i-0009000000-a22a23dbfe780a163a382017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 10V, Negative-QTOFsplash10-014i-0009000000-7907c6ab3ef19e9cdf862017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid ESI-TOF 30V, Negative-QTOFsplash10-014i-0009000000-847587fdc96a653e96512017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid LC-ESI-TOF , negative-QTOFsplash10-014i-0009000000-5c9df57aa4e8e48bd80f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid LC-ESI-TOF , negative-QTOFsplash10-014i-0009000000-a22a23dbfe780a163a382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid LC-ESI-TOF , negative-QTOFsplash10-014i-0009000000-847587fdc96a653e96512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-3c3e69329be8a71480762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid 30V, Positive-QTOFsplash10-014i-0009000000-847587fdc96a653e96512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid 30V, Negative-QTOFsplash10-014i-0009000000-7bccb707d42bca681a582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetracosanoic acid 10V, Positive-QTOFsplash10-014i-0009000000-a22a23dbfe780a163a382021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 10V, Positive-QTOFsplash10-0udi-0009000000-48bd2e6f8cbaa8fda6bd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 20V, Positive-QTOFsplash10-0kmi-2339000000-6881995e14be93cee8032015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 40V, Positive-QTOFsplash10-0a4l-6982000000-bcce0a5d41ac456500c72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 10V, Negative-QTOFsplash10-014i-0009000000-249bc2a1e0da9132abb12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 20V, Negative-QTOFsplash10-01ba-0009000000-bb2e8d3e4fc1a5f88c772015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetracosanoic acid 40V, Negative-QTOFsplash10-0a4l-9113000000-18bb969031b0d8959a2f2015-04-25Wishart 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
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.262 +/- 0.014 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.930 +/- 0.194 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified16.683 +/- 12.478 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  4. 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004651
KNApSAcK IDC00001223
Chemspider ID10724
KEGG Compound IDC08320
BioCyc IDTETRACOSANOATE
BiGG ID2218057
Wikipedia LinkLignoceric_acid
METLIN ID6427
PubChem Compound11197
PDB IDNot Available
ChEBI ID28866
Food Biomarker OntologyNot Available
VMH IDLGNC
MarkerDB IDNot Available
Good Scents IDrw1287001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Galloway JH, Cartwright IJ, Bennett MJ: Abnormal myocardial lipid composition in an infant with type II glutaric aciduria. J Lipid Res. 1987 Mar;28(3):279-84. [PubMed:3572253 ]
  2. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8. [PubMed:15565636 ]
  3. Petroni A, Blasevich M, Uziel G: Effects of the testosterone metabolite dihydrotestosterone and 5 alpha-androstan-3 alpha,17 beta-diol on very long chain fatty acid metabolism in X-adrenoleukodystrophic fibroblasts. Life Sci. 2003 Aug 8;73(12):1567-75. [PubMed:12865096 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name:
ACSL1
Uniprot ID:
P33121
Molecular weight:
77942.685