A branched-chain acyl CoA and intermediate in L-leucine metabolism
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Isovaleryl-Coenzyme A (sodium salt)

Item No. 39999

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-(3-methylbutanoate) coenzyme A, sodium salt
Synonyms
  • Isovaleryl-CoA
Molecular Formula
C26H44N7O17P3S • XNa
Formula Weight
851.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@H]([C@@H]1O[P](O)(O)=O)[C@@H](O[C@@H]1CO[P](O[P](OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(CC(C)C)=O)=O)=O)(O)=O)(O)=O)N2C3=NC=NC(N)=C3N=C2.[Na]
InChi Code
InChI=1S/C26H44N7O17P3S.Na/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33;/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41);/t15-,19-,20-,21+,25-;/m1./s1
InChi Key
MIOHTOXKBKMCMT-WADKRTIVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $36

    Add

    5 mg

    $168

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Isovaleryl-coenzyme A (isovaleryl-CoA) is a branched-chain acyl CoA and an intermediate in the metabolism of the essential amino acid L-leucine (Item No. 34342).1,2 It is formed from L-leucine by the branched-chain α-keto acid dehydrogenase (BCKAD) complex and is converted to 3-methylcrotonyl-CoA by isovaleryl-CoA dehydrogenase (IVD), an enzyme involved in the inborn error of metabolism isovaleric acidemia.3 Isovaleryl-CoA increases the oxidation rate of the branched-chain 2-oxo acids 3-methyl-2-butanoate and 4-methyl-2-oxopentanoate in isolated rat muscle mitochondria in the absence of carnitine when used at a concentration of 1 mM.4 It also inhibits succinate-CoA ligase activity in rat liver mitochondria (IC50 = 273 µM).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duan, Y., Li, F., Li, Y., et al. The role of leucine and its metabolites in protein and energy metabolism. Amino Acids 48(1), 41-51 (2016).

    2. Mohsen, A.-W.A., Anderson, B.D., Volchenboum, S.L., et al. Characterization of molecular defects in isovaleryl-CoA dehydrogenase in patients with isovaleric acidemia. Biochemistry 37(28), 10325-10335 (1998).

    3. Mack, M., Schniegler-Mattox, U., Peters, V., et al. Biochemical characterization of human 3-methylglutaconyl-CoA hydratase and its role in leucine metabolism. FEBS J. 273(9), 2012-2022 (2006).

    4. Veerkamp, J.H., van Moerkerk, H.T.B., and Wagenmakers, A.J.M. Interaction of short-chain and branched-chain fatty acids and their carnitine and CoA esters and of various metabolites and agents with branced-chain 2-oxo acid oxidation in rat muscle and liver mitochondria. Int. J. Biochem. 17(9), 967-974 (1985).

    5. Bergen, B.J., Stumpf, D.A., Haas, R., et al. A mechanism of toxicity of isovaleric acid in rat liver mitochondria. Biochem. Med. 27(2), 154-160 (1982).