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2-C-Methyl-D-erythritol-2,4-cyclodiphosphate (M2MDB000611)

Record Information
Version2.0
Creation Date2012-05-31 14:05:06 -0600
Update Date2015-06-03 15:54:44 -0600
Secondary Accession Numbers
  • ECMDB04103
Identification
Name:2-C-Methyl-D-erythritol-2,4-cyclodiphosphate
Description2-c-methyl-D-erythritol-2,4-cyclodiphosphate 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-C-Methyl-D-erythritol-2,4-cyclodiphosphoric acid
  • ME-2,4cPP
  • MeEry2,4CP
Chemical Formula:C5H10O9P2
Weight:Average: 276.075
Monoisotopic: 275.980004942
InChI Key:SFRQRNJMIIUYDI-UHNVWZDZSA-L
InChI:InChI=1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11)/p-2/t4-,5+/m1/s1
CAS number:143488-44-2
IUPAC Name:(6S,7R)-7-hydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2lambda5,4lambda5-trioxadiphosphocane-2,4-bis(olate)
Traditional IUPAC Name:(6S,7R)-7-hydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2lambda5,4lambda5-trioxadiphosphocane-2,4-bis(olate)
SMILES:[H][C@@]1(O)COP([O-])(=O)OP([O-])(=O)O[C@@]1(C)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility54.6 g/LALOGPS
logP-1ALOGPS
logP-1.8ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area148.41 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.84 m³·mol⁻¹ChemAxon
Polarizability19.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Flavodoxin reduced + Hydrogen ion >2 flavodoxin semi oxidized + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water
2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol <> 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Cytidine monophosphate
2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Reduced ferredoxin + Oxidized ferredoxin <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water +2 Oxidized ferredoxin + Reduced ferredoxin
2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > Cytidine monophosphate + 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + Oxidized-ferredoxins < 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Hydrogen ion + Reduced-ferredoxins
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > Cytidine monophosphate + 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Cytidine monophosphate
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
2 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol <>2 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Cytidine monophosphate
2 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Reduced ferredoxin + Oxidized ferredoxin <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water
2 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol <>2 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Cytidine monophosphate
SMPDB Pathways:
Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway)PW000975 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisPW000958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0570-7970000000-9e120133948f567c4eb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008a-3910000000-5dcada1fca7c8514646aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-744acdeec7f0eb28fcd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-0890000000-f1627213072237479c59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-5790000000-47b787782b958bd69d50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9400000000-7b8b6f0443210e85ef1eView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18425
HMDB IDNot Available
Pubchem Compound ID21605869
Kegg IDC11453
ChemSpider ID10241147
Wikipedia ID2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate
BioCyc ID2C-METH-D-ERYTHRITOL-CYCLODIPHOSPHATE
EcoCyc ID2C-METH-D-ERYTHRITOL-CYCLODIPHOSPHATE

Enzymes

Protein Details
1. 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
General function:
Involved in 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity
Specific function:
Converts 4-diphosphocytidyl-2-C-methyl-D-erythritol 2- phosphate into 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP) and CMP. Also converts 4-diphosphocytidyl-2-C-methyl-D- erythritol into 2-C-methyl-D-erythritol 3,4-cyclophosphate and CMP
Gene Name:
ispF
Uniprot ID:
P62617
Molecular weight:
16897
Reactions
2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP.
Protein Details
2. 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase
General function:
Involved in catalytic activity
Specific function:
Converts 2C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-2,4cPP) into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate
Gene Name:
ispG
Uniprot ID:
P62620
Molecular weight:
40683
Reactions
(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H(2)O + 2 oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin.
Protein Details
3. Flavodoxin-2
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential)
Gene Name:
fldB
Uniprot ID:
P0ABY4
Molecular weight:
19700
Protein Details
4. Flavodoxin-1
General function:
Involved in FMN binding
Specific function:
Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
Gene Name:
fldA
Uniprot ID:
P61949
Molecular weight:
19737