Pantetheine

Not to be confused with pantethine.

Pantetheine is the cysteamine amide analog of pantothenic acid (vitamin B₅). The dimer of this compound, pantethine is more commonly known, and is considered to be the most potent form of vitamin B₅. Pantetheine is an intermediate in the catabolism of coenzyme A by the body.^[1][2][3]

Pantetheine

Stereo, skeletal formula of pantetheine (R)
Names
Systematic IUPAC name (2R)-2,4-Dihydroxy-3,3-dimethyl-N-{3-oxo-3-[(2-sulfanylethyl)amino]propyl}butanamide
Other names Pantetheine
Identifiers
CAS Number	496-65-1 R Y
3D model (JSmol)	Interactive image
Beilstein Reference	1714196 R
ChEBI	CHEBI:16753 N
ChemSpider	466 Y 388453 R N
ECHA InfoCard	100.007.114
EC Number	207-824-1
KEGG	C00831 N
MeSH	Pantetheine
PubChem CID	479 439322 R
UNII	VCH6X4IARE R Y
InChI InChI=1S/C11H22N2O4S/c1-11(2,7-14)9(16)10(17)13-4-3-8(15)12-5-6-18/h9,14,16,18H,3-7H2,1-2H3,(H,12,15)(H,13,17) Y Key: ZNXZGRMVNNHPCA-UHFFFAOYSA-N Y
SMILES CC(C)(CO)C(O)C(=O)NCCC(=O)NCCS
Properties
Chemical formula	C11H22N2O4S
Molar mass	278.37 g·mol−1
Related compounds
Related compounds	Pantethine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Metabolism

Pantetheine is the product of dephosphorylation of phosphopantetheine:

phosphopantetheine → pantetheine + P_i

In E. coli, this reaction is catalyzed by for example alkaline phosphatase.^[4] The reverse reaction, phosphopantetheine synthesis, is catalyzed by various kinases:^[5]

phosphopantetheine + ATP → pantetheine + ADP

These kinases are able to act upon pantothenoic acid as well and are present in both microorganisms and animal livers.^[5]

Pantetheine is degraded by pantetheinase, which splits it into cysteamine and pantothenic acid:^[3]

pantetheine → cysteamine + pantothenate

Prebiotic evolution

Since pantetheine is a part of coenzyme A, a common cofactor, it is thought to have been present in prebiotic soup. A synthesis mechanism has also been suggested.^[6]