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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 13:07:46 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004149
Secondary Accession Numbers
  • HMDB04149
Metabolite Identification
Common NamePalmitelaidoyl-CoA
DescriptionPalmitelaidoyl-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. Palmitelaidoyl-CoA has been shown to inhibit oxidative phosphorylation in human cells which has implications for long-chain fatty acid disorders (PMID: 12538075 , 16020546 , 16651524 , 7662716 ).
Structure
Data?1582752300
Synonyms
ValueSource
Palmitelaidoyl CoAHMDB
Palmitelaidoyl coenzyme AHMDB
Palmitelaidoyl-coenzyme AHMDB
trans-9-Hexadecenoyl CoAHMDB
trans-9-Hexadecenoyl coenzyme AHMDB
trans-9-Hexadecenoyl-CoAHMDB
trans-9-Hexadecenoyl-coenzyme AHMDB
CoA(16:1(9E))HMDB
Palmitelaidoyl-CoAHMDB
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-[(9E)-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 Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(9E)-hexadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number62358-02-5
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-HQCBLXLFSA-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
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Imidolactam
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Carbonyl group
  • Alcohol
  • Organosulfur compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP2.33ALOGPS
logP0.24ChemAxon
logS-2.8ALOGPS
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
Polarizability100.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+233.44830932474
DeepCCS[M-H]-231.79530932474
DeepCCS[M-2H]-266.82930932474
DeepCCS[M+Na]+240.11430932474
AllCCS[M+H]+291.432859911
AllCCS[M+H-H2O]+292.032859911
AllCCS[M+NH4]+290.832859911
AllCCS[M+Na]+290.632859911
AllCCS[M-H]-297.032859911
AllCCS[M+Na-2H]-303.032859911
AllCCS[M+HCOO]-309.632859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 10V, Positive-QTOFsplash10-0udi-9000000000-f107abe30cc76fa0cbb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 20V, Positive-QTOFsplash10-000i-3701100449-1daebfa666f3d861ba162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 40V, Positive-QTOFsplash10-0002-0101900000-678f9a53fb23aa18a2182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 10V, Negative-QTOFsplash10-0udi-9000000000-4677fa0a81e9ed6f8bdb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 20V, Negative-QTOFsplash10-0ug0-9010201301-01a8ca4b0d0831d2bbfa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Palmitelaidoyl-CoA 40V, Negative-QTOFsplash10-004i-4101300209-c05bc6d50f95049cd9292021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB023321
KNApSAcK IDNot Available
Chemspider ID103883399
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131841371
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceStudies on long chain cis- and trans-acyl-CoA esters and acyl-CoA dehydrogenase from rat heart mitochondria. Korsrud, G. O.; Conacher, H. B. S.; Jarvis, G. A.; Beare-Rogers, J. L. Health Prot. Branch, Health Welfare Canada, Ottawa, ON, Can.
Material Safety Data Sheet (MSDS)Not Available
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 ]
  3. Ventura FV, Ruiter JP, Ijlst L, Almeida IT, Wanders RJ: Inhibition of oxidative phosphorylation by palmitoyl-CoA in digitonin permeabilized fibroblasts: implications for long-chain fatty acid beta-oxidation disorders. Biochim Biophys Acta. 1995 Aug 15;1272(1):14-20. [PubMed:7662716 ]
  4. Wolfgang MJ, Kurama T, Dai Y, Suwa A, Asaumi M, Matsumoto S, Cha SH, Shimokawa T, Lane MD: The brain-specific carnitine palmitoyltransferase-1c regulates energy homeostasis. Proc Natl Acad Sci U S A. 2006 May 9;103(19):7282-7. Epub 2006 May 1. [PubMed:16651524 ]