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CDP-Ethanolamine (YMDB00389)

Identification
YMDB IDYMDB00389
NameCDP-Ethanolamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCDP-ethanolamine belongs to the class of organic compounds known as cdp-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5'-diphosphate moiety attached to the oxygen. CDP-ethanolamine exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on CDP-ethanolamine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • cdp ethanolamine
  • CDP-ethanolamine
  • CDPethanolamine
  • cytidine diphosphate ethanolamine
  • Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) ester
  • Cytidine 5'-(trihydrogen diphosphoric acid), p'-(2-aminoethyl) ester
  • Cytidine diphosphoric acid ethanolamine
  • CDP Ethanolamine, p'-(32)P-labeled
  • Cytidine 5'-diphosphate ethanolamine
  • Cytidine 5'-diphosphoethanolamine
  • Cytidine 5’-diphosphate ethanolamine
  • Cytidine 5’-diphosphoethanolamine
  • Cytidine diphosphoethanolamine
CAS number3036-18-8
WeightAverage: 446.2442
Monoisotopic: 446.060380526
InChI KeyWVIMUEUQJFPNDK-PEBGCTIMSA-N
InChIInChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1
IUPAC Name(2-aminoethoxy)[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name2-aminoethoxy({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
Chemical FormulaC11H20N4O11P2
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=C([H])C(=NC1=O)N([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])C([H])([H])N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as cdp-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5'-diphosphate moiety attached to the oxygen.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentCDP-ethanolamines
Alternative Parents
Substituents
  • Cdp-ethanolamine
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Phosphoethanolamine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary amine
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP-1.7ALOGPS
logP-4.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area237.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity100.14 m³·mol⁻¹ChemAxon
Polarizability37.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Ether lipid metabolismPW002492 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ether lipid metabolismec00565 Map00565
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
1-O-Hexadecyl-2-palmitoyl-sn-glycerol + CDP-Ethanolamine → Cytidine monophosphate + 1-hexadecyl-2-palmitoyl-glycero-3-phosphoethanolamine
DG(16:0/16:0/0:0) + CDP-Ethanolamine → Cytidine monophosphate + hydron + PE(16:0/16:0)
O-Phosphoethanolamine + hydron + Cytidine triphosphate → CDP-Ethanolamine + Pyrophosphate
KEGG Reactions
CDP-Ethanolamine + DG(16:0/16:0/0:0) ↔ PE(14:0/16:1(9Z)) + Cytidine monophosphate + hydron
hydron + Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolamine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6793400000-ac76da0c6087752db3c9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00pj-8972160000-fd358ed61430e64ed4e0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-0002-0000900000-0b86b2b2cfc17d95ff90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-0002-1012900000-c5804a13d813a5377b79JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-0032-8157900000-36b36bcbce04a95bf962JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-004i-9122000000-f9d8d35bd43030c78e8bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 35V, negativesplash10-004i-9100000000-8db373393648433147a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-004i-9100000000-1cb47f991b97749fba0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, negativesplash10-004i-9000000000-4a5fcad27ccf2ff23957JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, negativesplash10-004i-9000000000-6b08787f67155728185fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-001i-0029000000-1668461b10d942d91cf9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9300000000-8eef8ed8fdaa72ae58a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-03fr-1390000000-88ee14c068713b4ad543JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-00di-0290000000-3006b045a5e65ff5fa52JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-4a998d56bcc8853cc4aeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-0002-3012900000-be071eccb64015240644JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-004i-9124300000-5d5dc9798e172dc0a1e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 78V, negativesplash10-004i-9100000000-c769c60b7993983641f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 92V, negativesplash10-004i-9100000000-1837fdf24962abbe6805JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-001i-0009000000-0d7a52eebf0db4a36d24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-001i-2129000000-a4a5a49c30ed6207c333JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5910100000-2a4aae3a59f3f928bc14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-7900000000-70f4dc43398ae42bd718JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9700000000-2d6893ab115d449880c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gvk-1512900000-bd91f3bd3454ae8dc4daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0n4i-6942200000-8c75516485feb49d2fa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5900000000-624299483014ca3a86f4JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kim, K., Kim, K. H., Storey, M. K., Voelker, D. R., Carman, G. M. (1999). "Isolation and characterization of the Saccharomyces cerevisiae EKI1 gene encoding ethanolamine kinase." J Biol Chem 274:14857-14866.10329685
  • Hjelmstad, R. H., Bell, R. M. (1988). "The sn-1,2-diacylglycerol ethanolaminephosphotransferase activity of Saccharomyces cerevisiae. Isolation of mutants and cloning of the EPT1 gene." J Biol Chem 263:19748-19757.2848840
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16732
HMDB IDHMDB01564
Pubchem Compound ID123727
Kegg IDC00570
ChemSpider ID110296
FOODB IDFDB022691
Wikipedia IDNot Available
BioCyc IDCDP-ETHANOLAMINE

Enzymes

Protein Details
1. Choline/ethanolaminephosphotransferase 1
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl ethanolamine to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the ethanolaminephosphotransferase might participate in the transport process. EPT1 catalyzes both choline- and ethanolamine-phosphotransferase reactions
Gene Name:
EPT1
Uniprot ID:
P22140
Molecular weight:
44559.30078
Reactions
CDP-ethanolamine + 1,2-diacylglycerol → CMP + a phosphatidylethanolamine.
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
Protein Details
2. Ethanolamine-phosphate cytidylyltransferase
General function:
Involved in catalytic activity
Specific function:
CTP + ethanolamine phosphate = diphosphate + CDP-ethanolamine
Gene Name:
MUQ1
Uniprot ID:
P33412
Molecular weight:
36862.60156
Reactions
CTP + ethanolamine phosphate → diphosphate + CDP-ethanolamine.