Isopentenyl pyrophosphate

Isopentenyl pyrophosphate
Names


IUPAC name (hydroxy-(3-methylbut-3-enoxy) phosphoryl)oxyphosphonic acid
Identifiers
CAS Number	358-71-4^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:128769^Y
ChemSpider	13115335^Y
MeSH	isopentenyl+pyrophosphate
PubChem	15983957
InChI InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)/p-3^Y Key: NUHSROFQTUXZQQ-UHFFFAOYSA-K^Y InChI=1/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)/p-3 Key: NUHSROFQTUXZQQ-DFZHHIFOAI
SMILES CC(=C)CCOP(=O)([O-])OP(=O)([O-])[O-]
Properties
Chemical formula	C₅H₁₂O₇P₂
Molar mass	246.092
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway), and is used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from acetyl-CoA via the mevalonate pathway (the "upstream" part), and then is isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase.

IPP can be synthesized via the alternative, non-mevalonate pathway of isoprenoid biosynthesis instead, where it is formed from (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by the enzyme HMB-PP reductase (LytB, IspH). The non-mevalonate pathway is utilized by many bacteria, apicomplexan protozoa such as malaria parasites, and the plastids of higher plants.