| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Source | Endogenous metabolite |
| Molecular weight | |
| Molecular formula | C25H40N7O17P3S |
| Activity | |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Crotonyl-CoA is a high-energy acyl donor that serves as an intermediate in the fermentation of butyric acid and in the metabolism of lysine and tryptophan, and it is also involved more broadly in the metabolism of fatty acids and amino acids. It acts as a substrate for p300's histone crotonyltransferase activity, competing with acetyl-CoA in p300-mediated histone acylation reactions, and it regulates global and gene-specific histone crotonylation levels in cells, with changes in its cellular concentration altering histone crotonylation at regulatory elements of activated genes. It also serves as the substrate for crotonyl-CoA reductase/carboxylase (CCRC)-catalyzed, NADPH-mediated reduction and carbon dioxide trapping that forms unusual alkylmalonyl-CoA polyketide synthase extender units, and it can be used to research the LPS-induced inflammatory response[1][2]. It is an endogenous metabolite with the molecular formula C25H40N7O17P3S and a molecular weight of 835.61 g/mol.
Physical & Chemical Properties
| CAS Number | 992-67-6 |
|---|---|
| Molecular Formula | C25H40N7O17P3S |
| Molecular Weight | 835.61 g/mol |
| Structure Classification | Others |
| SMILES | NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](OP(O)(O)=O)[C@@H](COP(OP(OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(/C=C/C)=O)=O)=O)(O)=O)(O)=O)O3 |
| Signaling Pathway | Metabolic Enzyme/Protease; Epigenetics |
| Bioactivity Class | Human Endogenous Metabolite |
| Initial Source | Endogenous metabolite |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
Crotonyl-CoA stimulates transcription directly in a cell-free system, more potently than acetylation, producing 1.66-fold more transcript[1]. When cellular Crotonyl-CoA concentrations are raised by sodium crotonate treatment at 2.5 mM, 5 mM, and 10 mM (12 h), global H3K18Cr levels in HeLa S3 cells increase in a dose-dependent manner[1]. In RAW 264.7 cells, raising cellular Crotonyl-CoA concentrations by sodium crotonate pretreatment at 0 mM, 2.5 mM, 5 mM, and 10 mM (6 h before 2 h of LPS stimulation) enhanced H3K18Cr at de novo-activated gene promoters and increased expression of those genes upon LPS stimulation[1]. Conversely, lowering cellular Crotonyl-CoA levels by ACSS2 knockdown (72 h before 2 h of LPS stimulation) decreased H3K18Cr at promoters of de novo-activated genes and attenuated their expression after LPS stimulation in RAW 264.7 cells[1].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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