| Record Information |
| Version |
3.5 |
| Creation Date |
2006-08-13 01:51:07 -0600 |
| Update Date |
2013-03-26 13:38:41 -0600 |
| HMDB ID |
HMDB03944 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
trans-2-Hexenoyl-CoA |
| Description |
trans-Hexenoyl-CoA is an intermediate in fatty acid metabolism. Beta-oxidation occurs in both mitochondria and peroxisomes. Mitochondria catalyze the beta-oxidation of the bulk of short-, medium-, and long-chain fatty acids derived from diet, and this pathway constitutes the major process by which fatty acids are oxidized to generate energy. Peroxisomes are involved in the beta-oxidation chain shortening of long-chain and very-long-chain fatty acyl-coenzyme (CoAs), long-chain dicarboxylyl-CoAs, the CoA esters of eicosanoids, 2-methyl-branched fatty acyl-CoAs, and the CoA esters of the bile acid intermediates di- and trihydroxycoprostanoic acids, and in the process they generate H2O2. Long-chain and very-long-chain fatty acids (VLCFAs) are also metabolized by the cytochrome P450 CYP4A omega-oxidation system to dicarboxylic acids that serve as substrates for peroxisomal beta-oxidation. The peroxisomal beta-oxidation system consists of (a) a classical peroxisome proliferator-inducible pathway capable of catalyzing straight-chain acyl-CoAs by fatty acyl-CoA oxidase, L-bifunctional protein, and thiolase, and (b) a second noninducible pathway catalyzing the oxidation of 2-methyl-branched fatty acyl-CoAs by branched-chain acyl-CoA oxidase (pristanoyl-CoA oxidase/trihydroxycoprostanoyl-CoA oxidase), D-bifunctional protein, and sterol carrier protein (SCP)x. trans-Hexenoyl-CoA is the substrate of the enzymes enoyl-coenzyme A reductase, acyl-CoA oxidase [EC 1.3.99.2-1.3.3.6], acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13], and Oxidoreductases [EC 1.3.99.-]; trans-Hexenoyl-CoA is an intermediate in fatty acid elongation in mitochondria, being the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74]. (PMID: 11375435 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (2E)-Hexenoyl-CoA
- (2E)-Hexenoyl-Coenzyme A
- trans-2,3-Dehydrohexanoyl-CoA
- trans-2,3-Dehydrohexanoyl-Coenzyme A
- trans-Hex-2-enoyl-CoA
- trans-Hex-2-enoyl-Coenzyme A
|
| Chemical Formula |
C27H44N7O17P3S |
| Average Molecular Weight |
863.661 |
| Monoisotopic Molecular Weight |
863.172723243 |
| IUPAC Name |
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-hex-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 IUPAC Name |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-hex-2-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 Number |
10018-93-6 |
| SMILES |
CCC\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/C27H44N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h6-7,14-16,20-22,26,37-38H,4-5,8-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/b7-6+/t16-,20-,21-,22?,26-/m1/s1 |
| InChI Key |
OINXHIBNZUUIMR-DOSZRKKKSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
Acyl 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 Parent |
Acyl CoAs |
| Ontology |
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Lipid biosynthesis, Fatty acid transport
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
-2.181 |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
Not Available
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Fatty acid Metabolism |
SMP00051
|
map00071
|
| Fatty Acid Elongation In Mitochondria |
SMP00054
|
map00062
|
| Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids |
SMP00480
|
Not Available
|
| Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids |
SMP00481
|
Not Available
|
|
| Normal Concentrations |
|
Not Available |
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023263 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
4444331  |
| KEGG Compound ID |
C05271  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB03944  |
| Metagene Link |
HMDB03944  |
| METLIN ID |
Not Available |
| PubChem Compound |
5280765  |
| PDB ID |
Not Available |
| ChEBI ID |
28706  |
| References |
| Synthesis Reference |
Tamvakopoulos, Constantine S.; Anderson, Vernon E. Detection of acyl-coenzyme A thioester intermediates of fatty acid b-oxidation as the N-acylglycines by negative-ion chemical ionization gas chromatography mass spectrometry. Analytical Biochemistry (1992), 200(2), 381-7. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |