Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:54:20 UTC |
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Update Date | 2016-11-09 01:21:20 UTC |
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Accession Number | CHEM035585 |
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Identification |
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Common Name | (S)-3-Hydroxyhexadecanoyl-CoA |
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Class | Small Molecule |
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Description | (S)-3-Hydroxyhexadecanoyl-CoA, also known as b-hydroxypalmitoyl-coenzyme A or (s)-(s)-(s)-3-hydroxyhexadecanoyl-coa, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms (S)-3-Hydroxyhexadecanoyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa) (S)-3-Hydroxyhexadecanoyl-CoA exists in all living organisms, ranging from bacteria to humans. In cattle, (S)-3-hydroxyhexadecanoyl-CoA is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF long 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-Hydroxyhexadecanoyl-coenzyme A | HMDB | (S)-3-Hydroxypalmitoyl-coenzyme A | HMDB | b-Hydroxypalmitoyl-CoA | HMDB | b-Hydroxypalmitoyl-coenzyme A | HMDB | beta-Hydroxypalmitoyl-CoA | HMDB | beta-Hydroxypalmitoyl-coenzyme A | HMDB | DL-3-Hydroxyhexadecanoyl-S-coenzyme A | HMDB | DL-3-Hydroxyhexadecanoyl-scoa | HMDB | DL-3-Hydroxyhexadecanoyl-Scoenzyme A | HMDB | S-(3-Hydroxyhexadecanoate | HMDB | S-(3-Hydroxyhexadecanoate)coenzyme A | HMDB | S-(3-Hydroxyhexadecanoic acid | HMDB | S-DL-3-Hydroxyhexadecanoate | HMDB | S-DL-3-Hydroxyhexadecanoic acid | HMDB | 3-Hydroxyhexadecanoyl-CoA | HMDB | 3-Hydroxyhexadecanoyl-coenzyme A | HMDB |
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Chemical Formula | C37H66N7O18P3S |
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Average Molecular Mass | 1021.942 g/mol |
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Monoisotopic Mass | 1021.340 g/mol |
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CAS Registry Number | 35106-50-4 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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Traditional Name | [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid |
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SMILES | CCCCCCCCCCCCC[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/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32?,36+/m0/s1 |
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InChI Key | DEHLMTDDPWDRDR-QQOJFMBSSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. |
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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 | Long-chain fatty acyl 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 | Not Available |
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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-4903110201-5c625add946cedeba8fd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0913130000-d6cef11122d96c9fb376 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000100-8d7d4b3ad4d074a7843f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0g1i-9670331410-7d32679c05799895d716 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-4920201000-cd5080910a861d80fc42 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-6900100000-fbfb99f57376aea60156 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fk9-9000000001-05072eea992abb5f2395 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01yc-3000100098-6c40c412026538d46263 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-0101490000-0ed7def0065ebb0477bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-30c47ac3be95c4e52760 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0l90-9200101220-df47e7774864d969c394 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fbm-9305604617-7125cce3b8fd55475b9c | 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 | 1D NMR | 1H 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 | HMDB0003932 |
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FooDB ID | FDB023251 |
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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 | 389498 |
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ChEBI ID | 27402 |
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PubChem Compound ID | 440600 |
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Kegg Compound ID | C05258 |
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YMDB ID | Not Available |
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ECMDB ID | ECMDB03932 |
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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. 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. | 2. 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. | 3. Hunt MC, Solaas K, Kase BF, Alexson SE: Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. J Biol Chem. 2002 Jan 11;277(2):1128-38. Epub 2001 Oct 22. | 4. Ventura FV, Ruiter JP, Ijlst L, de Almeida IT, Wanders RJ: Inhibitory effect of 3-hydroxyacyl-CoAs and other long-chain fatty acid beta-oxidation intermediates on mitochondrial oxidative phosphorylation. J Inherit Metab Dis. 1996;19(2):161-4. | 5. Ventura FV, Ruiter JP, Ijlst L, Almeida IT, Wanders RJ: Inhibition of oxidative phosphorylation by palmitoyl-CoA in digitonin permeabilized fibroblasts: implications for long-chain fatty acid beta-oxidation disorders. Biochim Biophys Acta. 1995 Aug 15;1272(1):14-20. |
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