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Record Information
Version1.0
Creation Date2016-05-26 05:54:53 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035597
Identification
Common Name(2E)-Hexadecenoyl-CoA
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(e)-C16:1 N-14-CoAHMDB
(e)-Hexadec-2-enoyl-CoA tetraanionHMDB
(e)-Hexadec-2-enoyl-coenzyme A tetraanionHMDB
(e)-Hexadec-2-enoyl-coenzyme A(4-)HMDB
trans-2-Hexadecenoyl-CoA(4-)HMDB
trans-2-Hexadecenoyl-coenzyme A tetraanionHMDB
trans-2-Hexadecenoyl-coenzyme A(4-)HMDB
trans-C16:1 N-14-CoAHMDB
trans-Hexadec-2-enoyl-CoA(4-)HMDB
(2E)-Hexadecenoyl-coenzyme AHMDB
trans-2-Hexadecenoyl-CoAHMDB
trans-2-Hexadecenoyl-coenzyme AHMDB
Chemical FormulaC37H60N7O17P3S
Average Molecular Mass999.895 g/mol
Monoisotopic Mass999.298 g/mol
CAS Registry Number4460-95-1
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(hexadec-2-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[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(hexadec-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
SMILESCCCCCCCCCCCCC\C=C\C(=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 IdentifierInChI=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/h16-17,24-26,30-32,36,47-48H,4-15,18-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/b17-16+/t26-,30-,31-,32+,36-/m1/s1
InChI KeyJUPAQFRKPHPXLD-MSHHSVQMSA-J
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 2-enoyl CoAs
Alternative Parents
Substituents
  • 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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.33 g/LALOGPS
logP2.38ALOGPS
logP0.83ChemAxon
logS-2.9ALOGPS
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
Refractivity237.74 m³·mol⁻¹ChemAxon
Polarizability100.03 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-000i-2902100102-e06fa4e929af2fe70271View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0923400000-0c41e8f5f297f48f3a2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900100000-68e3f194fa8c6130a574View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9872342603-867ca6273a57b1175f49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4931201001-79292093bdcf11aa8d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-d4910960caa05277f5d8View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003945
FooDB IDFDB023264
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45474
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID26332261
ChEBI ID61526
PubChem Compound ID5118010
Kegg Compound IDC05272
YMDB IDNot Available
ECMDB IDECMDB03945
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Al-Arif, Adhid; Blecher, Melvin. Chemical synthesis of carnitine and coenzyme A esters of the b-substituted intermediates of hexadecanoic acid metabolism. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1971), 248(3), 416-29.
2. Hinsch W, Klages C, Seubert W: On the mechanism of malonyl-CoA-independent fatty-acid synthesis. Different properties of the mitochondrial chain elongation and enoylCoA reductase in various tissues. Eur J Biochem. 1976 Apr 15;64(1):45-55.