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cerotic acid (YMDB00785)

Identification
YMDB IDYMDB00785
Namecerotic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionHexacosanoic acid, also known as C26:0 or N-hexacosanoate, 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. Hexacosanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexacosanoic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-hexyldecanoate
  • 1-hexyldecanoic acid
  • 1-Pentadecanecarboxylic acid
  • C16 fatty acid
  • C26:0
  • cerate
  • ceratinate
  • ceratinic acid
  • ceric acid
  • cerinate
  • cerinic acid
  • cerotate
  • cerotic acid
  • cerylate
  • cerylic acid
  • cetylic acid
  • CH3-[CH2]24-COOH
  • Coconut oil fatty acids
  • Hexacosansaeure
  • hexacosoic acid
  • Hexadecanoate
  • Hexadecanoic (palmitic) acid
  • hexadecanoic acid
  • Hexadecanoic acid (palmitic acid)
  • Hexadecanoic acid palmitic acid
  • Hexadecoate
  • Hexadecoic acid
  • hexadecylic acid
  • Hexaectylic acid
  • hexaeicosanoic acid
  • Hydrofol
  • n-C26:0
  • n-hexacosanoate
  • n-hexacosanoic acid
  • n-Hexadecanoate
  • n-Hexadecanoic acid
  • n-Hexadecoate
  • n-Hexadecoic acid
  • palmitate
  • palmitic acid
  • Palmitinate
  • Palmitinic acid
  • Palmitinsaeure
  • palmitoate
  • palmitoic acid
  • PAM
  • Pentadecanecarboxylate
  • Pentadecanecarboxylic acid
  • PLM
  • Cerotinic acid
  • Cerotinate
  • Hexacosoate
  • Hexaeicosanoate
  • Hexacosanoate
  • Hexacosanoate (N-C26:0)
  • Hexacosanoic acid
  • FA(26:0)
CAS number57-10-3
WeightAverage: 396.6899
Monoisotopic: 396.396730908
InChI KeyXMHIUKTWLZUKEX-UHFFFAOYSA-N
InChIInChI=1S/C26H52O2/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(27)28/h2-25H2,1H3,(H,27,28)
IUPAC Namehexacosanoic acid
Traditional IUPAC Namehexacosanoic acid
Chemical FormulaC26H52O2
SMILESCCCCCCCCCCCCCCCCCCCCCCCCCC(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 point61.8 °C
Experimental Properties
PropertyValueReference
Water Solubility4e-05 mg/mL at 25 oC [ROBB,ID (1966)]PhysProp
LogP7.17 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.8e-05 g/LALOGPS
logP9.87ALOGPS
logP10.7ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity123.09 m³·mol⁻¹ChemAxon
Polarizability55.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (docosanoyl)PW002408 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (icosanoyl)PW002434 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (stearoyl)PW002435 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)PW002404 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB ReactionsNot Available
KEGG Reactions
lignoceric acid + malonyl-CoA + hydron + NADPH → cerotic acid + Carbon dioxide + NADP + water + Coenzyme A
Adenosine triphosphate + cerotic acid + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + hexacosanoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900100000-dc0324482e5853e76290JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900100000-dc0324482e5853e76290JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900100000-dc0324482e5853e76290JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-9d83fa08f63878dd9794JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8890000000-a358b076f9e4d3b08976JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmr-9550000000-f90d4cc6a83ff8e16245JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4j-0109000000-bc2c74027165503fd92fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0pb9-2193000000-cf0ac4a96f99022c7b3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w30-6096000000-65025824de97c5fb5ff7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, negativesplash10-00lr-0009000000-998e2947790abd467bc7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0009000000-bd3c909a0431684b20e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug1-3439000000-ca5336c838aa14069626JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-6974000000-93ebd8f603ed3f48dd9dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-50e9c7751bdac41b78c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0009000000-fdc9aa019c323235312eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-af814ec2317a697df1a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-87ff11014d638fb7aeddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1009000000-28b98f74e9fa6d052c38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9003000000-9b4d6e9900769e9411a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2009000000-459e9bac675c0081de3dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-7039000000-16142145274003e6395dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-33f6f730f4cbdee5a975JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0597-9201000000-41113a5b904c5db7332dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID31009
HMDB IDHMDB00220
Pubchem Compound ID985
Kegg IDC00249
ChemSpider ID10037
FOODB IDFDB004035
WikipediaCerotic_acid
BioCyc IDCPD-8475

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).

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