Record Information
Version3.6
Creation Date2006-08-13 07:53:12 UTC
Update Date2013-02-09 00:12:51 UTC
HMDB IDHMDB03946
Secondary Accession Numbers
  • HMDB13082
Metabolite Identification
Common Name(2E)-Tetradecenoyl-CoA
Description(2E)-Tetradecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzymes acyl-CoA oxidase and Oxidoreductases [EC 1.3.3.6-1.3.99.-] and enzymes acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13]; (2E)-Tetradecenoyl-CoA is an intermediate in fatty acid elongation in mitochondria, being the substrate of the enzyme trans-2-enoyl-CoA reductase (NADPH) [EC 1.3.1.38]. (KEGG).
Structure
Thumb
Synonyms
  1. (2E)-Tetradecenoyl-CoA
  2. (2E)-Tetradecenoyl-Coenzyme A
  3. Trans-tetra-dec-2-enoyl-CoA
  4. Trans-tetra-dec-2-enoyl-CoA.
  5. Trans-tetra-dec-2-enoyl-Coenzyme A
  6. Trans-tetra-dec-2-enoyl-Coenzyme A.
  7. trans-Tetradec-2-enoyl-CoA
  8. trans-Tetradec-2-enoyl-Coenzyme A
Chemical FormulaC35H60N7O17P3S
Average Molecular Weight975.874
Monoisotopic Molecular Weight975.297923755
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-tetradec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-tetradec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number38795-33-4
SMILES
CCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(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/C35H60N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h14-15,22-24,28-30,34,45-46H,4-13,16-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/b15-14+/t24-,28-,29-,30?,34-/m1/s1
InChI KeyMBCVYCOKMMMWLX-IKUURZALSA-N
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 3',5' Bisphosphate
  • 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
LogP1.419Not Available
Predicted Properties
PropertyValueSource
water solubility1.93 g/LALOGPS
logP1.9ALOGPS
logP-1.2ChemAxon
logS-2.7ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count17ChemAxon
hydrogen donor count9ChemAxon
polar surface area363.63ChemAxon
rotatable bond count31ChemAxon
refractivity228.54ChemAxon
polarizability95.68ChemAxon
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 IDFDB023265
KNApSAcK IDNot Available
Chemspider ID4444333
KEGG Compound IDC05273
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03946
Metagene LinkHMDB03946
METLIN IDNot Available
PubChem Compound5280767
PDB IDNot Available
ChEBI ID27721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 114 proteins in total.

Enzymes

Gene Name:
ACAA1
Uniprot ID:
P09110
Gene Name:
ACADL
Uniprot ID:
P28330
Reactions
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Gene Name:
ACADM
Uniprot ID:
P11310
Reactions
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Gene Name:
ACOX1
Uniprot ID:
Q15067
Reactions
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-CoA + FADHdetails
Gene Name:
ACOX3
Uniprot ID:
O15254
Reactions
Tetradecanoyl-CoA + FAD unknown (2E)-Tetradecenoyl-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-Hydroxytetradecanoyl-CoA unknown (2E)-Tetradecenoyl-CoA + Waterdetails
Gene Name:
ECHS1
Uniprot ID:
P30084
Reactions
(S)-3-Hydroxytetradecanoyl-CoA unknown (2E)-Tetradecenoyl-CoA + Waterdetails
Gene Name:
HADHA
Uniprot ID:
P40939
Reactions
(S)-3-Hydroxytetradecanoyl-CoA unknown (2E)-Tetradecenoyl-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
Tetradecanoyl-CoA + NADP unknown (2E)-Tetradecenoyl-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 114 proteins in total.