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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:02 UTC
Update Date2019-07-23 07:13:54 UTC
HMDB IDHMDB0060244
Secondary Accession Numbers
  • HMDB60244
Metabolite Identification
Common NamePhosphodimethylethanolamine
DescriptionPhosphomonomethylethanolamine, phosphodimethylethanolamine and phosphocholine were weak competitive inhibitors of the cytidylyltransferase catalyzed reaction when phosphoethanolamine was used as a substrate, with Ki values of 7.0, 6.8 and 52.9 mM, respectively. (PMID: 8130268 ) Unlike the plant and Plasmodium PEAMT, which catalyze all three methylations in the pathway, PMT-2 catalyzes only the last two steps in the pathway, i.e., the methylation of phosphomonomethylethanolamine (P-MME) to phosphodimethylethanolamine (P-DME) and of P-DME to phosphocholine. (PMID: 16681378 )
Structure
Data?1563866034
Synonyms
ValueSource
2-Dimethylaminoethyl phosphateChEBI
Demanyl phosphateChEBI
Phosphoric acid, mono(2-(dimethylamino)ethyl) esterChEBI
2-Dimethylaminoethyl phosphoric acidGenerator
Demanyl phosphoric acidGenerator
Phosphate, mono(2-(dimethylamino)ethyl) esterGenerator
N,N-Dimethylethanolamine phosphoric acidHMDB
PhosphodimethylethanolamineChEBI
Chemical FormulaC4H12NO4P
Average Molecular Weight169.1161
Monoisotopic Molecular Weight169.050394389
IUPAC Name[2-(dimethylamino)ethoxy]phosphonic acid
Traditional Namephosphodimethylethanolamine
CAS Registry NumberNot Available
SMILES
CN(C)CCOP(O)(O)=O
InChI Identifier
InChI=1S/C4H12NO4P/c1-5(2)3-4-9-10(6,7)8/h3-4H2,1-2H3,(H2,6,7,8)
InChI KeyBLHVJAAEHMLMOI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphoethanolamines
Alternative Parents
Substituents
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility36 g/LALOGPS
logP10(-0.68) g/LALOGPS
logP10(-2.1) g/LChemAxon
logS10(-0.67) g/LALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.15 m³·mol⁻¹ChemAxon
Polarizability15.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.40731661259
DarkChem[M-H]-131.25431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phosphodimethylethanolamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9100000000-5563175fafe0d0209e8b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphodimethylethanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphodimethylethanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 10V, Positive-QTOFsplash10-00di-9200000000-e7028756c0d669985f672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 20V, Positive-QTOFsplash10-00di-9000000000-8802e50ab1fa29c442242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 40V, Positive-QTOFsplash10-05fr-9000000000-b89bb10484c6cbcb49562017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 10V, Negative-QTOFsplash10-016r-8900000000-6b56025ee9dabf37410e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 20V, Negative-QTOFsplash10-004i-9000000000-51826d746774a14c940d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 40V, Negative-QTOFsplash10-004i-9000000000-c69b6c4810af52f210b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 10V, Positive-QTOFsplash10-00di-9100000000-cb511d5dc0cc08a80cdd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 20V, Positive-QTOFsplash10-00di-9000000000-c286143495e50fa10a8d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 40V, Positive-QTOFsplash10-00di-9000000000-b8d5c5307bb9b2b32ab82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 10V, Negative-QTOFsplash10-002b-9000000000-b625a344980c82cc7f172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphodimethylethanolamine 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13482
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151438
PDB IDNot Available
ChEBI ID31997
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Vermeulen PS, Geelen MJ, van Golde LM: Substrate specificity of CTP: phosphoethanolamine cytidylyltransferase purified from rat liver. Biochim Biophys Acta. 1994 Mar 24;1211(3):343-9. [PubMed:8130268 ]
  3. Palavalli LH, Brendza KM, Haakenson W, Cahoon RE, McLaird M, Hicks LM, McCarter JP, Williams DJ, Hresko MC, Jez JM: Defining the role of phosphomethylethanolamine N-methyltransferase from Caenorhabditis elegans in phosphocholine biosynthesis by biochemical and kinetic analysis. Biochemistry. 2006 May 16;45(19):6056-65. [PubMed:16681378 ]