You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-24 18:48:06 UTC
Secondary Accession Numbers
  • HMDB01338
Metabolite Identification
Common NamePalmityl-CoA
DescriptionPalmityl-coa, also known as S-hexadecanoate or palmitoyl-coenzyme a, is a member of the class of compounds known as long-chain fatty acyl coas. Long-chain fatty acyl coas are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Palmityl-coa can be found primarily throughout most human tissues. Within the cell, palmityl-coa is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Palmityl-coa exists in all living species, ranging from bacteria to humans. In humans, palmityl-coa is involved in several metabolic pathways, some of which include cardiolipin biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)), cardiolipin biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z)), cardiolipin biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0), and cardiolipin biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)). Palmityl-coa is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/16:0/21:0), de novo triacylglycerol biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), de novo triacylglycerol biosynthesis tg(i-20:0/16:0/i-15:0), and de novo triacylglycerol biosynthesis TG(16:0/18:0/20:1(11Z)). Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis..
Hexadecanoyl CoAHMDB
Hexadecanoyl coenzyme AHMDB
Palmitoyl CoAHMDB
Palmitoyl coenzyme AHMDB
Palmitoyl-coenzyme AHMDB
Palmityl-coenzyme AHMDB
S-Hexadecanoate CoAHMDB
S-Hexadecanoate coenzyme AHMDB
S-Hexadecanoic acidHMDB
S-Palmitoylcoenzyme AHMDB
Chemical FormulaC37H66N7O17P3S
Average Molecular Weight1005.943
Monoisotopic Molecular Weight1005.344873947
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number1763-10-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Biological Location:


  Organ and components:

  Tissue and substructures:

  Cell and elements:


  Biofluid and excreta:




Route of exposure:



Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.74 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 Count34ChemAxon
Refractivity236.65 m³·mol⁻¹ChemAxon
Polarizability100.19 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-2902100202-8995491c4408cb9cd2ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0923300000-25204cd16c15043e7553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900100100-10cdb45f6d139ab32fe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fa9-9882342503-dc9f6ae4b03147f90b41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0040-3921201001-8e28a440bd4fa5cf4e70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-e25d7582c34ed6bb66cfView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • Brain
  • Erythroid Cells
  • Fibroblasts
  • Heart
  • Kidney
  • Liver
  • Lung
  • Muscle
  • Neuron
  • Pancreas
  • Placenta
  • Skeletal Muscle
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)Pw027831Pw027831 greyscalePw027831 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))Pw027832Pw027832 greyscalePw027832 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)Pw027833Pw027833 greyscalePw027833 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))Pw027834Pw027834 greyscalePw027834 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))Pw027835Pw027835 greyscalePw027835 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 IDFDB022562
KNApSAcK IDNot Available
Chemspider ID14902
KEGG Compound IDC00154
BiGG ID34063
Wikipedia LinkNot Available
PubChem Compound15667
PDB IDNot Available
ChEBI ID15525
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
  2. Gohil K, Jones DA, Edwards RH: Fatty acid oxidation in mitochondria from needle biopsy samples of human skeletal muscle. Clin Sci (Lond). 1984 Feb;66(2):173-8. [PubMed:6319070 ]
  3. Berge RK, Hagen LE, Farstad M: Isolation of palmitoyl-CoA hydrolases from human blood platelets. Biochem J. 1981 Dec 1;199(3):639-47. [PubMed:6122441 ]
  4. Casteels M, Schepers L, Parmentier G, Eyssen HJ, Mannaerts GP: Activation and peroxisomal beta-oxidation of fatty acids and bile acid intermediates in liver from Bombina orientalis and from the rat. Comp Biochem Physiol B. 1989;92(1):129-32. [PubMed:2706931 ]
  5. Carroll JE, McGuire BS, Hall CL: Fatty acyl-CoA dehydrogenase enzymes in human skeletal muscle. Clin Chim Acta. 1986 Dec 30;161(3):327-33. [PubMed:3802539 ]
  6. Holloway GP, Bezaire V, Heigenhauser GJ, Tandon NN, Glatz JF, Luiken JJ, Bonen A, Spriet LL: Mitochondrial long chain fatty acid oxidation, fatty acid translocase/CD36 content and carnitine palmitoyltransferase I activity in human skeletal muscle during aerobic exercise. J Physiol. 2006 Feb 15;571(Pt 1):201-10. Epub 2005 Dec 15. [PubMed:16357012 ]
  7. Bakken AM, Farstad M: Identical subcellular distribution of palmitoyl-CoA and arachidonoyl-CoA synthetase activities in human blood platelets. Biochem J. 1989 Jul 1;261(1):71-6. [PubMed:2528345 ]
  8. Fukao T, Watanabe H, Orii K, Takahashi Y, Hirano A, Kondo T, Yamaguchi S, Aoyama T, Kondo N: Myopathic form of very-long chain acyl-coa dehydrogenase deficiency: evidence for temperature-sensitive mild mutations in both mutant alleles in a Japanese girl. Pediatr Res. 2001 Feb;49(2):227-31. [PubMed:11158518 ]
  9. Haughey NJ, Cutler RG, Tamara A, McArthur JC, Vargas DL, Pardo CA, Turchan J, Nath A, Mattson MP: Perturbation of sphingolipid metabolism and ceramide production in HIV-dementia. Ann Neurol. 2004 Feb;55(2):257-67. [PubMed:14755730 ]
  10. Tonsgard JH, Stephens JK, Rhead WJ, Penn D, Horwitz AL, Kirschner BS, Whitington PF, Berger S, Tripp ME: Defect in fatty acid oxidation: laboratory and pathologic findings in a patient. Pediatr Neurol. 1991 Mar-Apr;7(2):125-30. [PubMed:2059253 ]
  11. Wanders RJ, van Roermund CW, de Vries CT, van den Bosch H, Schrakamp G, Tager JM, Schram AW, Schutgens RB: Peroxisomal beta-oxidation of palmitoyl-CoA in human liver homogenates and its deficiency in the cerebro-hepato-renal (Zellweger) syndrome. Clin Chim Acta. 1986 Aug 30;159(1):1-10. [PubMed:2944672 ]

Only showing the first 10 proteins. There are 121 proteins in total.


General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
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:
Uniprot ID:
Molecular weight:

Only showing the first 10 proteins. There are 121 proteins in total.