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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:22:22 UTC
Secondary Accession Numbers
  • HMDB01114
Metabolite Identification
Common NameStearoyl-CoA
DescriptionStearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC and diacylglycerol acyltransferase (DGAT, EC, the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075 , 10998569 , Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.).
Octadecanoyl-coenzyme AHMDB
S-Octadecanoate CoAHMDB
S-Octadecanoate coenzyme AHMDB
S-Octadecanoic acidHMDB
S-Stearate CoAHMDB
S-Stearate coenzyme AHMDB
S-Stearoylcoenzyme AHMDB
Stearoyl coenzyme AHMDB
Stearoyl coenzyme A esterHMDB
Stearoyl-coenzyme AHMDB
Stearyl coenzyme AHMDB
Stearyl-coenzyme AHMDB
Chemical FormulaC39H70N7O17P3S
Average Molecular Weight1033.996
Monoisotopic Molecular Weight1033.376174075
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number362-66-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

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  Tissue and substructures:


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  Biofluid and excreta:


Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

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    Chemical reaction:


Industrial application:

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.95 g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity245.85 m³·mol⁻¹ChemAxon
Polarizability104.58 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4902010200-7bda8058c8f1f477173cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913140000-c5d7727f2a4eb2ce8fdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010000-d8406ea8fe36f8736f7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-9651431400-a2fe6767c7d15d4d3816View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5920210000-b2648994ee4ecec2c305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-55fb9ae203fadd900172View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Plasmalogen SynthesisThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022431
KNApSAcK IDNot Available
Chemspider ID388366
KEGG Compound IDC00412
BiGG ID1451385
Wikipedia LinkNot Available
PubChem Compound439229
PDB IDNot Available
ChEBI ID15541
Synthesis ReferenceBoiron F; Heape M A; Cassagne C Assay of stearoyl-CoA synthesis in microsomes from normal and Trembler mouse sciatic nerves. Neuroscience letters (1984), 48(1), 7-12.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Castro-Chavez F: Microarrays, antiobesity and the liver. Ann Hepatol. 2004 Oct-Dec;3(4):137-45. [PubMed:15657555 ]
  2. Miyazaki M, Ntambi JM: Role of stearoyl-coenzyme A desaturase in lipid metabolism. Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21. [PubMed:12538075 ]
  3. Sonnino S, Chigorno V: Ganglioside molecular species containing C18- and C20-sphingosine in mammalian nervous tissues and neuronal cell cultures. Biochim Biophys Acta. 2000 Sep 18;1469(2):63-77. [PubMed:10998569 ]

Only showing the first 10 proteins. There are 115 proteins in total.


General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Has a dehydrogenase activity on palmitoyl-CoA (C16:0) and stearoyl-CoA (C18:0). It is three times more active on palmitoyl-CoA then on stearoyl-CoA. Has little activity on octanoyl-CoA (C8:0), butyryl-CoA (C4:0) or isovaleryl-CoA (5:0)
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in oxidoreductase activity
Specific function:
Terminal component of the liver microsomal stearyl-CoA desaturase system, that utilizes O(2) and electrons from reduced cytochrome b5 to catalyze the insertion of a double bond into a spectrum of fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA.
Gene Name:
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Molecular weight:
Stearoyl-CoA + ferrocytochrome b5 + Oxygen + Hydrogen Ion → Oleoyl-CoA + ferricytochrome b5 + Waterdetails
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Reduces trans-2,3-stearoyl-CoA to stearoyl-CoA of long and very long chain fatty acids.
Gene Name:
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Molecular weight:
General function:
Involved in stearoyl-CoA 9-desaturase activity
Specific function:
Fatty acid delta-9-desaturase that introduces a double bond in fatty acyl-coenzyme A at the delta-9 position.
Gene Name:
Uniprot ID:
Molecular weight:
Stearoyl-CoA + ferrocytochrome b5 + Oxygen + Hydrogen Ion → Oleoyl-CoA + ferricytochrome b5 + Waterdetails
General function:
Involved in regulation of apoptosis
Specific function:
Participates in chain elongation of fatty acids. Has no 2,4-dienoyl-CoA reductase activity.
Gene Name:
Uniprot ID:
Molecular weight:
trans-Octadec-2-enoyl-CoA + NADPH + Hydrogen Ion → Stearoyl-CoA + NADPdetails
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. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in thiolester hydrolase 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. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
Uniprot ID:
Molecular weight:
Stearoyl-CoA + Water → Coenzyme A + Stearic aciddetails
General function:
Lipid transport and metabolism
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. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
Uniprot ID:
Molecular weight:
Stearoyl-CoA + Water → Coenzyme A + Stearic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in hydrolase activity
Specific function:
Coenzyme A diphosphatase that mediates the hydrolysis of a wide range of CoA esters, including choloyl-CoA and branched- chain fatty-acyl-CoA esters. At low substrate concentrations medium and long-chain fatty-acyl-CoA esters are the primary substrates
Gene Name:
Uniprot ID:
Molecular weight:


General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
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Molecular weight:

Only showing the first 10 proteins. There are 115 proteins in total.