(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate

(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate

Names
IUPAC name (E)-4-hydroxy-3-methylbut-2-enoxy-oxidophosphoryl phosphate
Other names (E)-4-hydroxy-dimethylallyl pyrophosphate HDMAPP (E)-4-Hydroxy-3-methyl-but-2-enyl diphosphate HMBDP
Identifiers
CAS Number	396726-03-7 N[ChemSpider]
3D model ( JSmol )	Interactive image Interactive image
ChEBI	CHEBI:15664 Y
ChEMBL	ChEMBL145233 Y
ChemSpider	4445244 Y
PubChem CID	21597501
InChI InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)/b5-2+ Y Key: MDSIZRKJVDMQOQ-GORDUTHDSA-N Y InChI=1/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)/b5-2+ Key: MDSIZRKJVDMQOQ-GORDUTHDBB
SMILES CC(=CCOP(=O)([O-])OP(=O)([O-])[O-])CO O=P(OP(=O)(O)O)(OC/C=C(/CO)C)O
Properties
Chemical formula	C5H12O8P2
Molar mass	262.091 g·mol−1
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

(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP or HMB-PP) is an intermediate of the MEP pathway (non-mevalonate pathway) of isoprenoid biosynthesis.^[1][2] The enzyme HMB-PP synthase (GcpE, IspG) catalyzes the conversion of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MEcPP) into HMB-PP. HMB-PP is then converted further to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH).

HMB-PP is an essential metabolite in most pathogenic bacteria including Mycobacterium tuberculosis as well as in malaria parasites, but is absent from the human host.^[3]

HMB-PP is the physiological activator ("