2-C-Methylerythritol 4-phosphate

2-C-Methyl-D-erythritol 4-phosphate
Names

IUPAC name 2-C-Methyl-D-erythritol 4-(dihydrogen phosphate)
Systematic IUPAC name (2R,3S)-2,3,4-Trihydroxy-3-methylbutyl dihydrogen phosphate
Other names 2-C-Methylerythritol 4-phosphate Methyl-D-erythritol phosphate
Identifiers
CAS Number	206440-72-4^N
3D model (JSmol)	Interactive image
Abbreviations	MEP
ChEBI	CHEBI:58262^Y
ChemSpider	10246067^Y
PubChem CID	443198
CompTox Dashboard (EPA)	DTXSID90332064
InChI InChI=1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/p-2/t4-,5+/m1/s1^Y Key: XMWHRVNVKDKBRG-UHNVWZDZSA-L^Y
SMILES CC(CO)(C(COP(=O)(O)O)O)O
Properties
Chemical formula	C₅H₁₃O₇P
Molar mass	216.126
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

Chemical compound

2-C-Methyl-D-erythritol 4-phosphate (MEP) is an intermediate on the MEP pathway (non-mevalonate pathway) of isoprenoid precursor biosynthesis.^[1] It is the first committed metabolite on that pathway on the route to IPP and DMAPP.

References

^ Takahashi S, Kuzuyama T, Watanabe H, Seto H (1998). "A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis". Proc. Natl. Acad. Sci. U.S.A. 95 (17): 9879–84. Bibcode:1998PNAS...95.9879T. doi:10.1073/pnas.95.17.9879. PMC 21430. PMID 9707569.

External links

2-C-methylerythritol+4-phosphate at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

Lanosterol
14-demethyllanosterol
4alpha-Methylzymosterol
Zymosterone
Zymosterol

From Cholesterol
to Steroid hormones

22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol
See here instead.

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol