Showing metabocard for Palmitoleyl CoA (BMDB0006532)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:06 UTC
Update Date2020-05-21 16:27:18 UTC
BMDB IDBMDB0006532
Secondary Accession Numbers
  • BMDB06532
Metabolite Identification
Common NamePalmitoleyl CoA
DescriptionPalmitoleyl-CoA, also known as palmitoleoyl CoA or CoA(16:1(9Z)), 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. Thus, palmitoleyl-CoA is considered to be a fatty ester. Based on a literature review a significant number of articles have been published on Palmitoleyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability100.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-9000000000-f107abe30cc76fa0cbb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3701100449-1daebfa666f3d861ba16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0101900000-678f9a53fb23aa18a218View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9000000000-4677fa0a81e9ed6f8bdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-9010201301-01a8ca4b0d0831d2bbfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4101300209-c05bc6d50f95049cd929View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006532
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
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(14:0/14:1(9Z)/0:0) + Palmitoleyl CoA → TG(14:0/14:1(9Z)/16:1(9Z))[iso6] + Coenzyme Adetails
DG(14:0/15:0/0:0) + Palmitoleyl CoA → TG(14:0/15:0/16:1(9Z)) + Coenzyme Adetails
DG(14:0/16:0/0:0) + Palmitoleyl CoA → TG(14:0/16:0/16:1(9Z)) + Coenzyme Adetails
DG(14:0/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(14:0/16:1(9Z)/16:1(9Z))[iso3] + Coenzyme Adetails
DG(14:1(9Z)/14:1(9Z)/0:0) + Palmitoleyl CoA → TG(14:1(9Z)/14:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/15:0/0:0) + Palmitoleyl CoA → TG(14:1(9Z)/15:0/16:1(9Z)) + Coenzyme Adetails
DG(14:1(9Z)/16:0/0:0) + Palmitoleyl CoA → TG(14:1(9Z)/16:0/16:1(9Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(14:1(9Z)/16:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(15:0/15:0/0:0) + Palmitoleyl CoA → TG(15:0/15:0/16:1(9Z)) + Coenzyme Adetails
DG(15:0/16:0/0:0) + Palmitoleyl CoA → TG(15:0/16:0/16:1(9Z)) + Coenzyme Adetails
DG(15:0/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(15:0/16:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(16:0/16:0/0:0) + Palmitoleyl CoA → TG(16:0/16:0/16:1(9Z)) + Coenzyme Adetails
DG(16:0/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(16:0/16:1(9Z)/16:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/16:1(9Z)/0:0) + Palmitoleyl CoA → TG(16:1(9Z)/16:1(9Z)/16:1(9Z))[iso] + Coenzyme Adetails