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Bovine Metabolome Database



Showing metabocard for Tiglyl-CoA (BMDB02054)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-05-22 15:17:34
Update Date 2009-05-05 20:59:03
Accession Number BMDB02054
Common Name Tiglyl-CoA
Description Tiglyl-CoA is a metabolite in the degradation of isoleucine to propionic acid pathway. A defect in the conversion of tiglyl-CoA to alpha-methyl-beta-hydroxybutyryl-CoA, results in episodic abdominal pain and acidosis in patients with Tiglic acidemia (OMIM 275190)
Synonyms
  1. (E)-2-Methylcrotonoyl-CoA
  2. 2-Methylcrotanoyl-CoA
  3. 2-methylbut-2-enoyl-CoA
  4. 2-methylcrotonoyl-CoA
  5. 2-methylcrotonyl-CoA
  6. Tiglyl-coenzyme A
  7. methylcrotonoyl-CoA
  8. methylcrotonyl-CoA
  9. tigloyl-CoA
  10. tiglyl-CoA
  11. trans-2-methylbut-2-enoyl-CoA
  12. (E)-2-Methylcrotonoyl-Coenzyme A
  13. 2-Methylcrotanoyl-Coenzyme A
  14. 2-methylbut-2-enoyl-Coenzyme A
  15. 2-methylcrotonoyl-Coenzyme A
  16. 2-methylcrotonyl-Coenzyme A
  17. methylcrotonoyl-Coenzyme A
  18. methylcrotonyl-Coenzyme A
  19. tigloyl-Coenzyme A
  20. trans-2-methylbut-2-enoyl-Coenzyme A
Chemical IUPAC Name [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-[2-[(Z)-2-methylbut-2-enoyl]sulfanylethylcarbamoyl]ethylcarbamoyl]propoxy]phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid
Chemical Formula C26H42N7O17P3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Coenzyme A Derivatives
Sub Class
  • Short chain acyl CoAs
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; primary amine; primary aromatic amine; secondary carboxylic acid amide; thiocarboxylic acid ester; phosphoric acid ester; alkene; aromatic compound; heterocyclic compound
Biofunction
  • Lipid biosynthesis, Fatty acid transport
Application
Source
  • Endogenous
Average Molecular Weight 849.635
Monoisotopic Molecular Weight 849.157104
Isomeric SMILES CC=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=C(N)N=CN=C12
Canonical SMILES CC=C(C)C(=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 C03345 Link Image
BioCyc ID TIGLYL-COA Link Image
BiGG ID 41674 Link Image
Wikipedia Link Tiglyl-CoA Link Image
METLIN ID 448 Link Image
PubChem Compound 439894 Link Image
PubChem Substance 6188 Link Image
ChEBI ID 15478 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20?,24-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.56 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -4
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.02 [Predicted by ALOGPS]; -5.2 [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 PDB File Show
Experimental PDB Structure
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
  • Cytoplasm (Predicted from LogP)
  • mitochondria
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Valine, Leucine and Isoleucine Degradation
HMDB Pathways
Name Valine, Leucine and Isoleucine Degradation
Image Show Link Image
KEGG Pathways
Name Valine, Leucine and Isoleucine Degradation
Image Show Link Image
SimCell Pathways
Name Valine, Leucine and Isoleucine Degradation
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Graph Show Link Image
SBML Download (XML) Link Image
General References
  1. Wikipedia Link Image