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Showing metabocard for Tetracosanoic acid (BMDB0002003)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:46 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0002003
Secondary Accession Numbers
  • BMDB02003
Metabolite Identification
Common NameTetracosanoic acid
DescriptionLignoceric acid, also known as tetraeicosanoate or CH3-[CH2]22-COOH, 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. Lignoceric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. Lignoceric acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.2 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.56ALOGPS
logP9.81ChemAxon
logS-7.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-9dedfb3583ae4e553948View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bf-9000000000-2ae141518702212751a7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-9dedfb3583ae4e553948View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-2826f8c66ba3647dda0fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-51ad38c3eba8f98c3565View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-6d38b4af18d7872e12a9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-0509000000-b590f3868a4aa3c86803View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0903000000-a6d1b482b61c2d36ee1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-4ef3dd8c92115a6d4e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-07bf-9000000000-2ae141518702212751a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-3c3e69329be8a7148076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0791000000-10ab351997f48e512657View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0791000000-10ab351997f48e512657View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004r-0791000000-10ab351997f48e512657View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-a22a23dbfe780a163a38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-7907c6ab3ef19e9cdf86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0009000000-847587fdc96a653e9651View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-a22a23dbfe780a163a38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-847587fdc96a653e9651View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-3c3e69329be8a7148076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0009000000-847587fdc96a653e9651View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0009000000-7bccb707d42bca681a58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-a22a23dbfe780a163a38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-48bd2e6f8cbaa8fda6bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2339000000-6881995e14be93cee803View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6982000000-bcce0a5d41ac456500c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-249bc2a1e0da9132abb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-18bb969031b0d8959a2fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0avl-9200000000-6a6f857b59886189b246View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Peroxisome
Biospecimen Locations
  • Fibroblasts
  • Liver
  • Mammary Gland
  • Milk
  • Oocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002003
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. 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. [PubMed:23438684 ]
  3. 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. [PubMed:19038946 ]

Enzymes

Enzyme Details
1. Long-chain-fatty-acid--CoA ligase ACSBG1
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the conversion of fatty acids such as long-chain and very long-chain fatty acids to their active form acyl-CoAs for both synthesis of cellular lipids, and degradation via beta-oxidation. Can activate diverse saturated, monosaturated and polyunsaturated fatty acids.
Gene Name:
ACSBG1
Uniprot ID:
Q2KHW5
Molecular weight:
80585.0
Reactions
Tetracosanoic acid + Adenosine triphosphate + Coenzyme A → Tetracosanoyl-CoA + ADPdetails