Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001868
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
Thumb
Synonyms:
  • 1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphoric acid
Chemical Formula: C5H9O8P2
Average Molecular Weight: 259.0677
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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 ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassIsoprenoid phosphates
Direct Parent Isoprenoid phosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility38.0 mg/mLALOGPS
logP-0.03ALOGPS
logP-0.98ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area142.01 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.53 m3·mol-1ChemAxon
Polarizability19.21 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2090000000-51e49488f61d06edbe1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9550000000-f08d24a56abc8b5ad6c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tu-9000000000-964be53a3c9d528eb85dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-d717b254a9c49609c017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9250000000-062a631a1f04c4f6b885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9100000000-b4ea4d9c4f23adda85feView in MoNA
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
External Links:
ResourceLink
CHEBI ID128753
HMDB IDNot Available
Pubchem Compound ID21597501
Kegg IDNot Available
ChemSpider ID10224038
Wikipedia IDNot Available
BioCyc IDNot Available