Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003502
Identification
Name: 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate
Description:2-C-Methyl-D-erythritol 2,4-cyclodiphosphate or MECDP is a highly unusual cyclodiphosphate-containing intermediate in the mevalonate-independent pathway to isopentenyl diphosphate and dimethylallyl diphosphate (i.e. isoprenoid biosynthesis). It is a product of the enzyme 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP) synthase which catalyzes the conversion of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to MECDP [PMID: 11786530]
Structure
Thumb
Synonyms:
  • (6S,7R)-2,4-dihydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2$l^{5},4$l^{5}-trioxadiphosphocan-7-ol
  • (6S,7R)-6-(Hydroxymethyl)-6-methyl-1,3,5,2,4-trioxadiphosphocane-2,4,7-triol 2,4-dioxide
  • 2-C-Methyl-D-erythritol 2,4-cyclodiphosphoric acid
  • 3-Methyl-1,2,3,4-tetrahydroxybutane-1,3-cyclic bisphosphate
  • 3-Methyl-1,2,3,4-tetrahydroxybutane-1,3-cyclic bisphosphoric acid
Chemical Formula: C5H12O9P2
Average Molecular Weight: 278.0909
Monoisotopic Molecular Weight: 277.995655006
InChI Key: SFRQRNJMIIUYDI-UHNVWZDZSA-N
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)/t4-,5+/m1/s1
CAS number: Not Available
IUPAC Name:(6S,7R)-2,4,7-trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2???4???trioxadiphosphocane-2,4-dione
Traditional IUPAC Name: 3-mthbcp
SMILES:[H][C@@]1(O)COP(O)(=O)OP(O)(=O)O[C@@]1(C)CO
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Organic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct Parent Organic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility21.4 mg/mLALOGPS
logP-0.81ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.08 m3·mol-1ChemAxon
Polarizability20.4 Å3ChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-01ti-6980000000-2910078abdb147fc13f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ea-4910000000-25d3520582e8fc1a1eeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-9aca2f6aa5f425257fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-1b1435063fd721a5b41eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u3-9440000000-28575060d57d85ca486cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9430000000-7e6056ba6fc2cfd9c792View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18425
HMDB IDNot Available
Pubchem Compound ID126747
Kegg IDC11453
ChemSpider ID112576
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoCDI