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Acetyl coenzyme A (Standard)

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CAS Number
72-89-9
UNSPSC Description
Acetyl coenzyme A (Standard) is the analytical standard of Acetyl coenzyme A. This product is intended for research and analytical applications. Acetyl-coenzyme A (Acetyl-CoA) is a membrane-impermeant central metabolic intermediate, participates in the TCA cycle and oxidative phosphorylation metabolism. Acetyl-coenzyme A, regulates various cellular mechanisms by providing (sole donor) acetyl groups to target amino acid residues for post-translational acetylation reactions of proteins. Acetyl Coenzyme A is also a key precursor of lipid synthesis[1][2][3][4].
Target Antigen
Autophagy; Endogenous Metabolite; Oxidative Phosphorylation
Type
Reference Standards
Related Pathways
Autophagy;Metabolic Enzyme/Protease
Field of Research
Metabolic Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/acetyl-coenzyme-a-standard.html
Smiles
O[C@H]1[C@@H](O[C@H](COP(OP(OCC(C)([C@@H](O)C(NCCC(NCCSC(C)=O)=O)=O)C)(O)=O)(O)=O)[C@H]1OP(O)(O)=O)N2C3=C(C(N)=NC=N3)N=C2
Molecular Weight
809.57
References & Citations
[1]Choudhary C, et al. The growing landscape of lysine acetylation links metabolism and cell signalling. Nat Rev Mol Cell Biol. 2014 Aug;15(8):536-50. |[2]Mariño G, et al. Regulation of autophagy by cytosolic acetyl-coenzyme A. Mol Cell. 2014 Mar 6;53(5):710-25. |[3]Zhu H, et al. Cardiac autophagy is a maladaptive response to hemodynamic stress. J Clin Invest. 2007 Jul;117(7):1782-93. |[4]Pietrocola F, et al. Acetyl coenzyme A: a central metabolite and second messenger. Cell Metab. 2015 Jun 2;21(6):805-21.
Shipping Conditions
Room temperature

Chemical Information

acetyl CoA

Acetyl-CoA is an acyl-CoA having acetyl as its S-acetyl component. It has a role as a coenzyme, an effector, an acyl donor and a fundamental metabolite. It is functionally related to a coenzyme A and an acetic acid. It is a conjugate acid of an acetyl-CoA(4-).

CAS Number72-89-9
PubChem CID444493
IUPAC NameS-[2-[3-[[(2R)-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] ethanethioate
Molecular FormulaC23H38N7O17P3S
Molecular Weight809.6
XLogP-5.6
Topological Polar Surface Area389
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count22
Rotatable Bond Count20
Heavy Atom Count51
Formal Charge0
Complexity1380
SMILES
CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
InChI
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
InChIKey
ZSLZBFCDCINBPY-ZSJPKINUSA-N
Chemical Structure
2D Structure
2D structure of acetyl CoA
CAS: 72-89-9
CID: 444493
Formula: C23H38N7O17P3S
MW: 809.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight809.6
XLogP3-5.6
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count22
Rotatable Bond Count20
Exact Mass809.12577494
Monoisotopic Mass809.12577494
Topological Polar Surface Area389 Ų
Heavy Atom Count51
Formal Charge0
Complexity1380
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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