Record Information
Version3.6
Creation Date2006-08-13 07:51:53 UTC
Update Date2013-05-29 19:39:14 UTC
HMDB IDHMDB03945
Secondary Accession Numbers
  • HMDB06533
Metabolite Identification
Common Name(2E)-Hexadecenoyl-CoA
Description(2E)-Hexadecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme enoyl-CoA hydratase [EC:4.2.1.17]; (2E)-Hexadecenoyl-CoA is also the substrate of the enzyme trans-2-enoyl-CoA reductase [EC:1.3.1.38], in the fatty acid elongation pathway in mitochondria. (PMID: 1278159 , KEGG).
Structure
Thumb
Synonyms
  1. (2E)-Hexadecenoyl-CoA
  2. (2E)-Hexadecenoyl-Coenzyme A
  3. trans-2-Hexadecenoyl-CoA
  4. trans-2-Hexadecenoyl-Coenzyme A
Chemical FormulaC37H60N7O17P3S
Average Molecular Weight999.895
Monoisotopic Molecular Weight999.297923755
IUPAC Name[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl {[(3R)-3-{[2-({2-[(2E)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl phosphonato]oxy}phosphonate
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl [(3R)-3-{[2-({2-[(2E)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl phosphonato]oxyphosphonate
CAS Registry Number4460-95-1
SMILES
CCCCCCCCCCCCC\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 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/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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Enone
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside Diphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct ParentAcyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.319Not Available
Predicted Properties
PropertyValueSource
water solubility1.22 g/LALOGPS
logP3.34ALOGPS
logP-0.26ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count17ChemAxon
hydrogen donor count5ChemAxon
polar surface area374.95ChemAxon
rotatable bond count33ChemAxon
refractivity233.25ChemAxon
polarizability98.77ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023264
KNApSAcK IDNot Available
Chemspider ID26332261
KEGG Compound IDC05272
BioCyc IDNot Available
BiGG ID45474
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03945
Metagene LinkHMDB03945
METLIN IDNot Available
PubChem Compound46173176
PDB IDNot Available
ChEBI ID61526
References
Synthesis ReferenceAl-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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. Pubmed: 1278159

Only showing the first 50 proteins. There are 115 proteins in total.

Enzymes

Gene Name:
ACAA1
Uniprot ID:
P09110
Gene Name:
ACADL
Uniprot ID:
P28330
Reactions
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Gene Name:
ACADM
Uniprot ID:
P11310
Reactions
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Gene Name:
ACOX1
Uniprot ID:
Q15067
Reactions
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Gene Name:
ACOX3
Uniprot ID:
O15254
Reactions
hexadecanoyl-CoA + FAD unknown (2E)-Hexadecenoyl-CoA + FADHdetails
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
DGAT1
Uniprot ID:
O75907
Gene Name:
SCD
Uniprot ID:
O00767
Gene Name:
EHHADH
Uniprot ID:
Q08426
Reactions
(S)-3-Hydroxyhexadecanoyl-CoA unknown (2E)-Hexadecenoyl-CoA + Waterdetails
Gene Name:
ECHS1
Uniprot ID:
P30084
Reactions
(S)-3-Hydroxyhexadecanoyl-CoA unknown (2E)-Hexadecenoyl-CoA + Waterdetails
Gene Name:
HADHA
Uniprot ID:
P40939
Reactions
(S)-3-Hydroxyhexadecanoyl-CoA unknown (2E)-Hexadecenoyl-CoA + Waterdetails
Gene Name:
SOAT2
Uniprot ID:
O75908
Gene Name:
SOAT1
Uniprot ID:
P35610
Gene Name:
ACSL4
Uniprot ID:
O60488
Gene Name:
ACSL1
Uniprot ID:
P33121
Gene Name:
ACSL6
Uniprot ID:
Q9UKU0
Gene Name:
ACSL5
Uniprot ID:
Q9ULC5
Gene Name:
ACSL3
Uniprot ID:
O95573
Gene Name:
MECR
Uniprot ID:
Q9BV79
Reactions
hexadecanoyl-CoA + NADP unknown (2E)-Hexadecenoyl-CoA + NADPH + Hydrogen Iondetails
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Gene Name:
ACOT8
Uniprot ID:
O14734
Gene Name:
SLC27A2
Uniprot ID:
O14975
Gene Name:
DBI
Uniprot ID:
P07108
Gene Name:
FABP3
Uniprot ID:
P05413
Gene Name:
SLC27A5
Uniprot ID:
Q9Y2P5
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2

Transporters

Only showing the first 50 proteins. There are 115 proteins in total.