lignoceric acid (YMDB00684)

Identification
YMDB IDYMDB00684
Namelignoceric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTetracosanoic 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. Based on a literature review a significant number of articles have been published on Tetracosanoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Lignocerat
  • Lignocerate
  • Lignoceric acid
  • Lignozerinsaeure
  • n-Tetracosanoate
  • n-Tetracosanoic acid
  • tetracosanate
  • tetracosanic acid
  • Tetracosanoat
  • Tetracosanoate
  • tetracosanoic acid
  • Tetracosansaeure
  • tetracosoate
  • tetracosoic acid
  • tetraeicosanoate
  • tetraeicosanoic acid
  • tetraicosanoic acid
  • CH3-[CH2]22-COOH
  • Tetraicosanoate
  • Lignoceric acid, silver (1+) salt
  • Lignoceric acid, sodium salt
  • Lignoceric acid, potassium salt
  • Tetracosanoic acid, potassium salt (1:1)
  • Potassium tetracosanoate
  • FA(24:0)
CAS number557-59-5
WeightAverage: 368.6367
Monoisotopic: 368.36543078
InChI KeyQZZGJDVWLFXDLK-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Nametetracosanoic acid
Traditional IUPAC Namelignoceric acid
Chemical FormulaC24H48O2
SMILESCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
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
Physical Properties
StateSolid
Charge0
Melting point84.2 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cell Envelope
  • Cytoplasm
  • Endoplasmic Reticulum
  • Extracellular
  • Lipid Particle
  • Mitochondrion
  • Peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB ReactionsNot Available
KEGG Reactions
stearic acid + NADPH + hydron + malonyl-CoA → Coenzyme A + lignoceric acid + NADP + Carbon dioxide + water
lignoceric acid + malonyl-CoA + hydron + NADPH → cerotic acid + Carbon dioxide + NADP + water + Coenzyme A
Adenosine triphosphate + lignoceric acid + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + Tetracosanoyl-CoA
water + Tetracosanoyl-CoA → lignoceric acid + hydron + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-9dedfb3583ae4e553948JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bf-9000000000-2ae141518702212751a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-9dedfb3583ae4e553948JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-2826f8c66ba3647dda0fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-51ad38c3eba8f98c3565JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-6d38b4af18d7872e12a9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-0509000000-b590f3868a4aa3c86803JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0903000000-a6d1b482b61c2d36ee1dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-4ef3dd8c92115a6d4e0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-07bf-9000000000-2ae141518702212751a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-3c3e69329be8a7148076JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0791000000-10ab351997f48e512657JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0791000000-10ab351997f48e512657JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004r-0791000000-10ab351997f48e512657JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-a22a23dbfe780a163a38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-7907c6ab3ef19e9cdf86JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0009000000-847587fdc96a653e9651JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-a22a23dbfe780a163a38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-847587fdc96a653e9651JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-3c3e69329be8a7148076JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0009000000-847587fdc96a653e9651JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0009000000-7bccb707d42bca681a58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-a22a23dbfe780a163a38JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-48bd2e6f8cbaa8fda6bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2339000000-6881995e14be93cee803JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6982000000-bcce0a5d41ac456500c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-249bc2a1e0da9132abb1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-18bb969031b0d8959a2fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0avl-9200000000-6a6f857b59886189b246JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Matias, A. C., Pedroso, N., Teodoro, N., Marinho, H. S., Antunes, F., Nogueira, J. M., Herrero, E., Cyrne, L. (2007). "Down-regulation of fatty acid synthase increases the resistance of Saccharomyces cerevisiae cells to H2O2." Free Radic Biol Med 43:1458-1465.17936191
  • Hatch, G. M., Smith, A. J., Xu, F. Y., Hall, A. M., Bernlohr, D. A. (2002). "FATP1 channels exogenous FA into 1,2,3-triacyl-sn-glycerol and down-regulates sphingomyelin and cholesterol metabolism in growing 293 cells." J Lipid Res 43:1380-1389.12235169
  • Kohlwein, S. D., Eder, S., Oh, C. S., Martin, C. E., Gable, K., Bacikova, D., Dunn, T. (2001). "Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae." Mol Cell Biol 21:109-125.11113186
  • Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28866
HMDB IDHMDB02003
Pubchem Compound ID11197
Kegg IDC08320
ChemSpider ID10724
FOODB IDFDB004651
WikipediaLignoceric_acid
BioCyc IDTETRACOSANOATE

Enzymes

Protein Details
1. Elongation of fatty acids protein 2
General function:
Involved in fatty acid elongase activity
Specific function:
Involved in synthesis of 1,3-beta-glucan. Could be a subunit of 1,3-beta-glucan synthase. Could be also a component of the membrane bound fatty acid elongation systems that produce the 26-carbon very long chain fatty acids that are precursors for ceramide and sphingolipids. Appears to be involved in the elongation of fatty acids up to 24 carbons. Appears to have the highest affinity for substrates with chain length less than 22 carbons
Gene Name:
FEN1
Uniprot ID:
P25358
Molecular weight:
40001.80078
Reactions
Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).
Protein Details
2. Peroxisomal acyl-coenzyme A thioester hydrolase 1
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.

Transporters

Protein Details
1. Very long-chain fatty acid transport protein
General function:
Involved in catalytic activity
Specific function:
May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised
Gene Name:
FAT1
Uniprot ID:
P38225
Molecular weight:
77140.29688
Reactions