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	2012-10-10 12:17:09 -0600
Update Date	2015-06-03 17:25:57 -0600
Secondary Accession Numbers	ECMDB23112
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9bc069a8> Close
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
Weight:	Average: 278.0909 Monoisotopic: 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-1,3,5,2λ⁵,4λ⁵-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
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organic oxoanionic compounds
Sub Class	Organic pyrophosphates
Direct Parent	Organic pyrophosphates
Alternative Parents	Organic phosphoric acids and derivatives Secondary alcohols Polyols Oxacyclic compounds Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Organic pyrophosphate Organic phosphoric acid derivative Secondary alcohol Oxacycle Organoheterocyclic compound Polyol Organic oxide Hydrocarbon derivative Primary alcohol Organooxygen compound Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	tetritol phosphate (CHEBI:18425 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 21.4 g/L ALOGPS logP -0.81 ALOGPS logP -1.8 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.83 ChemAxon pKa (Strongest Basic) -3.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 142.75 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 49.08 m³·mol⁻¹ ChemAxon Polarizability 20.4 ų ChemAxon Number of Rings 1 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-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate + Cytidine monophosphate 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + 2 oxidized ferredoxin > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate +2 reduced ferredoxin 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate + Cytidine monophosphate + Cytidine monophosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01ti-6980000000-2910078abdb147fc13f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00ea-4910000000-25d3520582e8fc1a1eee View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9200000000-9aca2f6aa5f425257fca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0390000000-1b1435063fd721a5b41e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01u3-9440000000-28575060d57d85ca486c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9430000000-7e6056ba6fc2cfd9c792 View in MoNA MS Mass Spectrum (Electron Ionization) 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18425 HMDB ID Not Available Pubchem Compound ID 126747 Kegg ID C11453 ChemSpider ID Not Available Wikipedia ID 2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate BioCyc ID Not Available Ligand Expo CDI

Enzymes