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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
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility36 g/LALOGPS
logP-0.68ALOGPS
logP-2.1ChemAxon
logS-0.67ALOGPS
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

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available136.40731661259
DarkChem[M-H]-PredictedNot Available131.25431661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9100000000-5563175fafe0d0209e8b2017-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9200000000-e7028756c0d669985f672017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-8802e50ab1fa29c442242017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9000000000-b89bb10484c6cbcb49562017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-8900000000-6b56025ee9dabf37410e2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-51826d746774a14c940d2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c69b6c4810af52f210b52017-10-06View 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
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 ]