Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:44:26 UTC
Update Date2022-08-31 18:23:29 UTC
Metabolite IDMMDBc0031688
Metabolite Identification
Common Name1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate
Description1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate is a member of the chemical class known as Organic Pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate is an intermediate in the mehtylerithritol phosphate pathway. . D-glyceraldehyde-3-phosphate and pyruvate are initially combined to yield 1-deoxy-D-xylylose 5-phosphate (DXP). DXP is then rearranged and reduced to generate the pathway's namesake compound, 2-C-methyl-D-erythritol 4-phosphate (MEP). In the third reaction MEP is converted into 4-diphosphocytidyl-2-C-methylerythritol, which is subsequently phosphorylated at the 2 position hydroxy group, yielding 4-diphosphocytidyl-2C-methylerythritol 2-phosphate. This product is then converted into 2-C-methyl-D-erythritol 2,4-cyclodiphosphate. This compound is then reduced to generate 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. In the final step, this diphosphate compound is converted by a single enzyme into a 5-6:1 ratio of IPP and DMAPP This ratio is subsequently adjusted to 7:3 by isopentenyl diphosphate isomerase. Both IPP and DMAPP then become the basic building blocks of polyisoprenoid biosynthesis.
Structure
Synonyms
ValueSource
(2E)-4-Hydroxy-3-methylbut-2-enyl diphosphateChEBI
(2E)-4-Hydroxy-3-methylbut-2-enyl diphosphate trianionChEBI
(2E)-4-Hydroxy-3-methylbut-2-enyl pyrophosphate(3-)ChEBI
(e)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphateChEBI
HMBPPChEBI
(2E)-4-Hydroxy-3-methylbut-2-enyl diphosphoric acidGenerator
(2E)-4-Hydroxy-3-methylbut-2-enyl diphosphoric acid trianionGenerator
(2E)-4-Hydroxy-3-methylbut-2-enyl pyrophosphoric acid(3-)Generator
(e)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphoric acidGenerator
1-Hydroxy-2-methyl-2-(e)-butenyl 4-diphosphoric acidGenerator
Molecular FormulaC5H9O8P2
Average Mass259.0677
Monoisotopic Mass258.977265288
IUPAC Name{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl phosphonato]oxy}phosphonate
Traditional Namehmbpp
CAS Registry NumberNot Available
SMILES
[H]\C(COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CO
InChI Identifier
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)/p-3/b5-2+
InChI KeyMDSIZRKJVDMQOQ-GORDUTHDSA-K