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Bovine Metabolome Database



Showing metabocard for (S)-3-Hydroxyhexadecanoyl-CoA (BMDB03932)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-08-13 08:26:45
Update Date 2009-05-05 20:59:47
Accession Number BMDB03932
Common Name (S)-3-Hydroxyhexadecanoyl-CoA
Description (S)-3-Hydroxyhexadecanoyl-CoA is a beta-oxidation intermediate derivative of palmitoyl-CoA and the substrate of the enzyme peroxisomal acyl-CoA thioesterase 2 (PTE-2, EC 3.1.2.2), which is localized in the peroxisome. The peroxisomal beta-oxidation system contains two sets of enzymes, one of which is involved in the oxidation of branched chain fatty acids and intermediates in the hepatic bile acid biosynthetic pathway and consists of one or two branched-chain acyl-CoA oxidase(s), a D-specific bifunctional protein and the sterol carrier-like protein x (SCPx). Peroxisomes are cellular organelles present in all eukaryotic cells. They play an indispensable role in the metabolism of a variety of lipids including very long-chain fatty acids, dicarboxylic fatty acids, bile acids, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic fatty acids. (S)-3-Hydroxyhexadecanoyl-CoA may accumulate intracellularly in certain long-chain fatty acid/j-oxidation deficiencies. Succinate-driven synthesis of ATP from ADP and phosphate is progressively inhibited by increasing concentrations of (S)-3-Hydroxyhexadecanoyl-CoA. (PMID: 11673457, 8739955, 7662716)
Synonyms
  1. (S)-3-hydroxyhexadecanoyl-coenzyme A
  2. (S)-3-hydroxypalmitoyl-coenzyme A
  3. b-Hydroxypalmitoyl-CoA
  4. DL-3-Hydroxyhexadecanoyl-S-coenzyme A
  5. DL-3-Hydroxyhexadecanoyl-SCoA
  6. S-DL-3-hydroxyhexadecanoate
  7. S-(3-hydroxyhexadecanoate)coenzyme A
  8. b-Hydroxypalmitoyl-Coenzyme A
  9. beta-Hydroxypalmitoyl-CoA
  10. DL-3-Hydroxyhexadecanoyl-SCoenzyme A
  11. beta-Hydroxypalmitoyl-Coenzyme A
  12. S-DL-3-hydroxyhexadecanoic acid
  13. S-(3-hydroxyhexadecanoic acid
  14. S-(3-hydroxyhexadecanoate
Chemical IUPAC Name S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (3S)-3-hydroxyhexadecanethioate
Chemical Formula C37H66N7O18P3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Coenzyme A Derivatives
Sub Class
  • Long chain acyl CoAs
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; primary amine; primary aromatic amine; secondary carboxylic acid amide; thiocarboxylic acid ester; phosphoric acid ester; aromatic compound; heterocyclic compound
Biofunction
  • Lipid biosynthesis, Fatty acid transport
Application
Source
  • Endogenous
Average Molecular Weight 1021.942
Monoisotopic Molecular Weight 1021.339783
Isomeric 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
Canonical SMILES CCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
KEGG Compound ID C05258 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 440600 Link Image
PubChem Substance 7645 Link Image
ChEBI ID 27402 Link Image
CAS Registry Number 35106-50-4
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.14 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -4
State Solid
Experimental LogP/Hydrophobicity 1.481 Source: PhysProp
Predicted LogP/Hydrophobicity 1.68 [Predicted by ALOGPS]; -1.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Fatty Acid Elongation In Mitochondria
  • Fatty Acid Metabolism
HMDB Pathways
Name Fatty Acid Elongation In Mitochondria
Image Show Link Image
Name Fatty Acid Metabolism
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KEGG Pathways
Name Fatty Acid Elongation In Mitochondria
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Name Fatty Acid Metabolism
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SimCell Pathways
Name Fatty Acid Elongation In Mitochondria
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Graph
SBML
Name Fatty Acid Metabolism
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Graph
SBML
General References Not Available