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Identification
YMDB IDYMDB00785
Namecerotic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCerotic acid (hexacosanoic acid) is a saturated fatty acid. It has been documented in beeswax and carnauba wax.
Structure
Thumb
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)
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
Biosynthesis of unsaturated fatty acidsec01040 Map01040
Ether lipid metabolismec00565 Map00565
Fatty acid biosynthesisec00061 Map00061
Fatty acid elongation in mitochondriaec00062 Map00062
Fatty acid metabolismec00071 Map00071
SMPDB ReactionsNot Available
KEGG Reactions
lignoceric acid + malonyl-CoA + hydron + NADPHcerotic acid + Carbon dioxide + NADP + water + Coenzyme A
Adenosine triphosphate + cerotic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + hexacosanoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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

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