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Identification
YMDB IDYMDB00682
Namestearic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionStearic acid, also known as stearate or 18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Stearic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-Heptadecanecarboxylate
  • 1-Heptadecanecarboxylic acid
  • 18:0
  • 2-Oxooctadecanoic acid
  • 2-Oxostearate
  • acide octadecanoique
  • acide stearique
  • Barolub FTA
  • C18:0
  • Cetylacetic acid
  • ELA
  • Heptadecanecarboxylic acid
  • Isooctadecanoic acid
  • Isostearic acid
  • Macrogol ester
  • n-Octadecanoate
  • n-Octadecanoic acid
  • N-octadecanoic acidd
  • n-Octadecylic acid
  • Octadecanoate
  • octadecanoic acid
  • octadecanoic acid, ion(1-)
  • Octadecansaeure
  • Octadecoic acid
  • Oktadekansaeure
  • OLA
  • Pearl stearic
  • Promulsin
  • Proviscol wax
  • stearate
  • STEARIC ACID
  • stearic acid, ion(1-)
  • Stearinsaeure
  • Stearite
  • Stearophanate
  • Stearophanic acid
  • Steric acid
  • Vanicol
  • VCA
  • CH3-[CH2]16-COOH
  • Octadecoate
  • Stearex beads
  • Stearic acid cherry
  • Calcium stearate
  • Aluminum tristearate
  • Ammonium stearate
  • Zinc stearate
  • Magnesium stearate
  • Sodium stearate
  • Aluminum monostearate
  • FA(18:0)
CAS number57-11-4
WeightAverage: 284.4772
Monoisotopic: 284.271530396
InChI KeyQIQXTHQIDYTFRH-UHFFFAOYSA-N
InChIInChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
IUPAC Nameoctadecanoic acid
Traditional IUPAC Namestearic acid
Chemical FormulaC18H36O2
SMILESCCCCCCCCCCCCCCCCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • 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 point68.8 °C
Experimental Properties
PropertyValueReference
Water Solubility0.000597 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP8.23 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.6e-05 g/LALOGPS
logP8.02ALOGPS
logP7.15ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.29 m³·mol⁻¹ChemAxon
Polarizability38.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Peroxisome
Organoleptic Properties
Flavour/OdourSource
FattyFDB002941
MildFDB002941
OdorlessFDB002941
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 (tetracosanoyl-CoA)PW002404 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
stearoyl-CoA + waterhydron + Coenzyme A + stearic acid
KEGG Reactions
malonyl-CoA + hydron + NADPH + Palmitic acidstearic acid + Carbon dioxide + NADP + water + Coenzyme A
stearic acid + NADPH + hydron + malonyl-CoACoenzyme A + lignoceric acid + NADP + Carbon dioxide + water
stearic acid + Adenosine triphosphate + Coenzyme AAdenosine monophosphate + Pyrophosphate + stearoyl-CoA
stearoyl-CoA + waterstearic acid + hydron + Coenzyme A
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
  • Le Guedard, M., Bessoule, J. J., Boyer, V., Ayciriex, S., Velours, G., Kulik, W., Ejsing, C. S., Shevchenko, A., Coulon, D., Lessire, R., Testet, E. (2009). "PSI1 is responsible for the stearic acid enrichment that is characteristic of phosphatidylinositol in yeast." FEBS J 276:6412-6424.19796168
  • Petschnigg, J., Wolinski, H., Kolb, D., Zellnig, G., Kurat, C. F., Natter, K., Kohlwein, S. D. (2009). "Good fat, essential cellular requirements for triacylglycerol synthesis to maintain membrane homeostasis in yeast." J Biol Chem 284:30981-30993.19608739
  • Sakuradani, E., Murata, S., Kanamaru, H., Shimizu, S. (2008). "Functional analysis of a fatty acid elongase from arachidonic acid-producing Mortierella alpina 1S-4." Appl Microbiol Biotechnol 81:497-503.18795285
  • You, K. M., Rosenfield, C. L., Knipple, D. C. (2003). "Ethanol tolerance in the yeast Saccharomyces cerevisiae is dependent on cellular oleic acid content." Appl Environ Microbiol 69:1499-1503.12620835
  • 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
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28842
HMDB IDHMDB00827
Pubchem Compound ID5281
Kegg IDC01530
ChemSpider ID5091
FOODB IDFDB002941
WikipediaStearic_acid
BioCyc IDSTEARIC_ACID

Enzymes

General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:
FAA4
Uniprot ID:
P47912
Molecular weight:
77266.5
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
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).
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:
FAA1
Uniprot ID:
P30624
Molecular weight:
77865.79688
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:
FAA3
Uniprot ID:
P39002
Molecular weight:
77946.0
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.
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

General function:
Involved in transport
Specific function:
Involved in the import of activated long-chain fatty acids from the cytosol to the peroxisomal matrix
Gene Name:
PXA1
Uniprot ID:
P41909
Molecular weight:
100024.0