| Record Information |
| Version |
3.5 |
| Creation Date |
2006-08-13 01:51:53 -0600 |
| Update Date |
2013-02-08 17:12:51 -0700 |
| HMDB ID |
HMDB03945 |
| Secondary Accession Numbers |
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| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (2E)-Hexadecenoyl-CoA
- (2E)-Hexadecenoyl-Coenzyme A
- trans-2-Hexadecenoyl-CoA
- trans-2-Hexadecenoyl-Coenzyme A
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| Chemical Formula |
C37H60N7O17P3S |
| Average Molecular Weight |
999.895 |
| Monoisotopic Molecular Weight |
999.297923755 |
| 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 Number |
4460-95-1 |
| 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 Key |
JUPAQFRKPHPXLD-MSHHSVQMSA-J |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
Acyl CoAs |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
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| 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
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| Direct Parent |
Acyl CoAs |
| Ontology |
| Status |
Expected and Not Quantified |
| Origin |
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| 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
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| Cellular locations |
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| 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 |
2.319 |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Fatty acid Metabolism |
SMP00051
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map00071
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| Fatty Acid Elongation In Mitochondria |
SMP00054
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map00062
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| Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids |
SMP00482
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Not Available
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| Normal Concentrations |
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Not Available |
| Abnormal Concentrations |
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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 |
FDB023264 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
26332261  |
| KEGG Compound ID |
C05272  |
| BioCyc ID |
Not Available |
| BiGG ID |
45474  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB03945  |
| Metagene Link |
HMDB03945  |
| METLIN ID |
Not Available |
| PubChem Compound |
46173176  |
| PDB ID |
Not Available |
| ChEBI ID |
61526  |
| References |
| Synthesis Reference |
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. |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available |
| Enzymes |
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| Name: |
Peroxisomal acyl-coenzyme A oxidase 2
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| Reactions: |
- (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA + H2O + acceptor = (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26- oyl-CoA + reduced acceptor [RN:R07374]
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| Gene Name: |
ACOX2 |
| Uniprot ID: |
Q99424  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHB |
| Uniprot ID: |
P21953  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHA |
| Uniprot ID: |
P12694  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acyl-CoA desaturase
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| Reactions: |
- stearoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = oleoyl-CoA + 2 ferricytochrome b5 + 2 H2O [RN:R02222]
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| Gene Name: |
SCD |
| Uniprot ID: |
O00767  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Bile acyl-CoA synthetase
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| Reactions: |
- (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
- (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
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| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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