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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 14:52:36 UTC
Update Date2021-09-14 15:43:36 UTC
HMDB IDHMDB0006532
Secondary Accession Numbers
  • HMDB06532
Metabolite Identification
Common NamePalmitoleyl-CoA
DescriptionPalmitoleyl-CoA is a monounsaturated fatty acid, the product of palmitoyl-CoA from a reaction catalyzed by stearoyl-CoA desaturase (EC 1.14.99.5, SCD) in the endoplasmic reticulum, an enzyme that catalyzes the delta9-cis desaturation of saturated fatty acyl-CoAs. These monounsaturated fatty acids are used as substrates for the synthesis of triglycerides, wax esters, cholesteryl esters, and membrane phospholipids. The saturated to monounsaturated fatty acid ratio affects membrane phospholipid composition and alteration in this ratio has been implicated in a variety of disease states including cardiovascular disease, obesity, diabetes, neurological disease, skin disorders, and cancer. Thus, the expression of SCD is of physiological importance in normal and disease states. Unsaturated fatty acids are the most abundant form of stored fat in the human body and are vital for all living organisms. In addition to their role as an energy source, they are integral constituents of cell membranes, playing a role in membrane fluidity, cell signalling, and membrane integrity. Numerous beneficial physiologic effects have been attributed to unsaturated fatty acids, including protection from obesity, diabetes, cancer, and atherosclerosis (PMID: 12538075 , 16020546 ).
Structure
Data?1582752390
Synonyms
ValueSource
(Z)-9-Hexadecenoyl-CoAChEBI
cis-9-Hexadecenoyl-CoAChEBI
cis-9-Hexadecenoyl-coenzyme AChEBI
Palmitoleoyl-coenzyme AChEBI
Palmitoleyl-coenzyme AChEBI
Palmitoleoyl CoAHMDB
Palmitoleoyl coenzyme AHMDB
Palmitoleoyl-CoAHMDB
Palmitoleyl CoAHMDB
Palmitoleyl coenzyme AHMDB
cis-9-Hexadecenoyl CoAHMDB
cis-9-Hexadecenoyl coenzyme AHMDB
CoA(16:1(9Z))HMDB
Palmitoleyl-CoAChEBI
Chemical FormulaC37H64N7O17P3S
Average Molecular Weight1003.93
Monoisotopic Molecular Weight1003.329225797
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(9Z)-hexadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Namepalmitoleoyl-coa
CAS Registry Number18198-76-0
SMILES
CCCCCC\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/b10-9-/t26-,30-,31-,32+,36-/m1/s1
InChI KeyQBYOCCWNZAOZTL-MDMKAECGSA-N
Chemical Taxonomy
Description 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
Substituents
  • 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP10(2.33) g/LALOGPS
logP10(0.24) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity237.76 m³·mol⁻¹ChemAxon
Polarizability100.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 10V, Positive-QTOFsplash10-0udi-9000000000-f107abe30cc76fa0cbb82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 20V, Positive-QTOFsplash10-000i-3701100449-1daebfa666f3d861ba162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 40V, Positive-QTOFsplash10-0002-0101900000-678f9a53fb23aa18a2182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 10V, Negative-QTOFsplash10-0udi-9000000000-4677fa0a81e9ed6f8bdb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 20V, Negative-QTOFsplash10-0ug0-9010201301-01a8ca4b0d0831d2bbfa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitoleyl-CoA 40V, Negative-QTOFsplash10-004i-4101300209-c05bc6d50f95049cd9292021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
FooDB IDFDB023962
KNApSAcK IDNot Available
Chemspider ID23107132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25244394
PDB IDNot Available
ChEBI ID53152
Food Biomarker OntologyNot Available
VMH IDHDCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKorsrud, G. O.; Conacher, H. B. S.; Jarvis, G. A.; Beare-Rogers, J. L. Studies on long chain cis- and trans-acyl-CoA esters and acyl-CoA dehydrogenase from rat heart mitochondria. Lipids (1977), 12(2), 177-81.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Ensenauer R, He M, Willard JM, Goetzman ES, Corydon TJ, Vandahl BB, Mohsen AW, Isaya G, Vockley J: Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids. J Biol Chem. 2005 Sep 16;280(37):32309-16. Epub 2005 Jul 14. [PubMed:16020546 ]