2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate

2-C-Methyl-d-erythritol-2,4-cyclopyrophosphate (MEcPP) (also 2-C-Methyl-d-erythritol-2,4-cyclodiphosphate) is an intermediate in the MEP pathway (non-mevalonate) of isoprenoid precursor biosynthesis.^[1] MEcPP is produced by MEcPP synthase (IspF) and is a substrate for HMB-PP synthase (IspG).

2-C-Methyl-d-erythritol-2,4-cyclodiphosphate

Names
Systematic IUPAC name (6S,7R)-2,4,7-Trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ5,4λ5-trioxadiphosphocane-2,4-dione
Identifiers
CAS Number	151435-51-7 Y
3D model (JSmol)	Interactive image
ChemSpider	67
MeSH	2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate
PubChem CID	68
CompTox Dashboard (EPA)	DTXSID10931210 DTXSID60610886, DTXSID10931210
InChI InChI=1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11) Key: SFRQRNJMIIUYDI-UHFFFAOYSA-N
SMILES C[C@]1([C@H](COP(=O)(OP(=O)(O1)O)O)O)CO
Properties
Chemical formula	C5H12O9P2
Molar mass	278.09 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Under conditions of oxidative stress, MEcPP accumulates in certain bacteria.^[2] MEcPP releases histone-like proteins from DNA, triggering nucleoid decondensation in Chlamydia trachomatis during the process of terminal differentiation.^[3] Abiotic stresses to plants, including wounding and excessive high-light exposure, lead to an increase in MEcPP accumulation in chloroplasts. Transported from the chloroplast to the plant cell nucleus, MEcPP engages in retrograde signalling that leads to the specific induction of nuclear-encoded stress-response genes.^[4]