Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-08-09 09:25:04 -0600
Update Date	2015-06-03 17:21:35 -0600
Secondary Accession Numbers	ECMDB21473
Identification
Name:	1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate
Description	1-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb4fba874> Close
Synonyms:	1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphoric acid
Chemical Formula:	C5H9O8P2
Weight:	Average: 259.0677 Monoisotopic: 258.977265288
InChI Key:	MDSIZRKJVDMQOQ-GORDUTHDSA-K
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)/p-3/b5-2+
CAS number:	Not Available
IUPAC Name:	{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl phosphonato]oxy}phosphonate
Traditional IUPAC Name:	hmbpp
SMILES:	[H]\C(COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CO
Chemical Taxonomy
Description	belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Isoprenoid phosphates
Direct Parent	Isoprenoid phosphates
Alternative Parents	Organic pyrophosphates Alkyl phosphates Primary alcohols Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Organic pyrophosphate Isoprenoid phosphate Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Primary alcohol Organooxygen compound Alcohol Organic anion Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	organophosphate oxoanion (CHEBI:128753 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 38 g/L ALOGPS logP -0.03 ALOGPS logP -0.98 ChemAxon logS -0.92 ALOGPS pKa (Strongest Acidic) 1.77 ChemAxon pKa (Strongest Basic) -2.7 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 142.01 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 47.53 m³·mol⁻¹ ChemAxon Polarizability 19.21 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + a reduced flavodoxin > Water + Hydrogen ion + an oxidized flavodoxin + 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphate 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > NADP + Water + Dimethylallylpyrophosphate + Dimethylallylpyrophosphate
SMPDB Pathways:	Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway) PW000975 Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesis PW000958
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-2090000000-51e49488f61d06edbe1e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kr-9550000000-f08d24a56abc8b5ad6c5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05tu-9000000000-964be53a3c9d528eb85d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-0090000000-d717b254a9c49609c017 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-05fr-9250000000-062a631a1f04c4f6b885 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-003s-9100000000-b4ea4d9c4f23adda85fe View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 128753 HMDB ID Not Available Pubchem Compound ID 21597501 Kegg ID Not Available ChemSpider ID 10224038 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes