Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:54:45 UTC |
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Update Date | 2016-11-09 01:21:20 UTC |
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Accession Number | CHEM035594 |
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Identification |
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Common Name | (S)-Hydroxyhexanoyl-CoA |
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Class | Small Molecule |
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Description | (S)-Hydroxyhexanoyl-CoA, also known as (S)-3-hydroxycaproyl-coa, belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative. Thus, (S)-hydroxyhexanoyl-CoA is considered to be a fatty ester lipid molecule (S)-Hydroxyhexanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Hydroxyhexanoyl-CoA exists in all living species, ranging from bacteria to humans. In cattle, (S)-hydroxyhexanoyl-CoA is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF short chain saturated fatty acids pathway. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(S)-3-Hydroxycaproyl-CoA | ChEBI | (S)-3-Hydroxycaproyl-coenzyme A | ChEBI | 3-Hydroxyhexanoyl-coenzyme A | ChEBI | (S)-3-Hydroxyhexanoyl-CoA | Kegg | (S)-Hydroxyhexanoyl-CoA | ChEBI |
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Chemical Formula | C27H46N7O18P3S |
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Average Molecular Mass | 881.677 g/mol |
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Monoisotopic Mass | 881.183 g/mol |
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CAS Registry Number | 74875-70-0 |
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IUPAC Name | 4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid |
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Traditional Name | (S)-hydroxyhexanoyl-coa |
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SMILES | CCC[C@H](O)CC(=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=C(N)N=CN=C12 |
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InChI Identifier | InChI=1S/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22?,26+/m0/s1 |
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InChI Key | VAAHKRMGOFIORX-DWUFXMDISA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acyl thioesters |
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Direct Parent | (S)-3-hydroxyacyl CoAs |
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Alternative Parents | |
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Substituents | - Coenzyme a or derivatives
- Purine ribonucleoside 3',5'-bisphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside diphosphate
- Ribonucleoside 3'-phosphate
- Pentose phosphate
- Pentose-5-phosphate
- Beta amino acid or derivatives
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Imidolactam
- N-acyl-amine
- N-substituted imidazole
- Organic phosphoric acid derivative
- Monosaccharide
- Pyrimidine
- Alkyl phosphate
- Fatty amide
- Phosphoric acid ester
- Tetrahydrofuran
- Imidazole
- Azole
- Heteroaromatic compound
- Carbothioic s-ester
- Secondary alcohol
- Thiocarboxylic acid ester
- Carboxamide group
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Organosulfur compound
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Primary amine
- Organopnictogen compound
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-1912000130-9d32f1a7db66966548f9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0913000000-325a72f7e906068360b8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1911000000-391d16b13e4ae8bf53de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-5911140350-4d35b969b1c6af839051 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3910110010-ec218967cee87cdd7488 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-4900100000-f4b7577fa42ccd3e2dee | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-0000000090-b8add5209e54d6b6e866 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01pa-0500000290-e534ff3e17b57c33f0eb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-0029000000-3ad72154a1670e7077a7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000000090-22f1eaad51934a88d28c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00p0-7800102890-d08bf7452876ed8a38d2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002o-9302601610-9537bb62a975804266fc | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0003942 |
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FooDB ID | FDB030163 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 10140154 |
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ChEBI ID | 28276 |
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PubChem Compound ID | 11966160 |
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Kegg Compound ID | C05268 |
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YMDB ID | YMDB16169 |
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ECMDB ID | ECMDB03942 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. 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. Anal Biochem. 1992 Feb 1;200(2):381-7. Pubmed: 1632504 | 2. Dalluge JJ, Gort S, Hobson R, Selifonova O, Amore F, Gokarn R: Separation and identification of organic acid-coenzyme A thioesters using liquid chromatography/electrospray ionization-mass spectrometry. Anal Bioanal Chem. 2002 Nov;374(5):835-40. Epub 2002 Oct 8. | 3. Klees AG, Linder D, Buckel W: 2-Hydroxyglutaryl-CoA dehydratase from Fusobacterium nucleatum (subsp. nucleatum): an iron-sulfur flavoprotein. Arch Microbiol. 1992;158(4):294-301. | 4. Kim J, Hetzel M, Boiangiu CD, Buckel W: Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of alpha-amino acids by anaerobic bacteria. FEMS Microbiol Rev. 2004 Oct;28(4):455-68. | 5. Hofmeister AE, Buckel W: (R)-lactyl-CoA dehydratase from Clostridium propionicum. Stereochemistry of the dehydration of (R)-2-hydroxybutyryl-CoA to crotonyl-CoA. Eur J Biochem. 1992 Jun 1;206(2):547-52. | 6. Kuchta RD, Hanson GR, Holmquist B, Abeles RH: Fe-S centers in lactyl-CoA dehydratase. Biochemistry. 1986 Nov 18;25(23):7301-7. | 7. Kuchta RD, Abeles RH: Lactate reduction in Clostridium propionicum. Purification and properties of lactyl-CoA dehydratase. J Biol Chem. 1985 Oct 25;260(24):13181-9. | 8. Sokatch JR: Alanine and aspartate formation during growth on valine-C14 by Pseudomonas aeruginosa. J Bacteriol. 1966 Jul;92(1):72-5. | 9. Megraw RE, Reeves HC, Ajl SJ: Formation of lactyl-coenzyme A and pyruvyl-coenzyme A from lactic acid by Escherichia coli. J Bacteriol. 1965 Oct;90(4):984-8. |
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