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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:53 UTC
HMDB IDHMDB0001564
Secondary Accession Numbers
  • HMDB01564
Metabolite Identification
Common NameCDP-Ethanolamine
DescriptionCytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond.
Structure
Thumb
Synonyms
ValueSource
CDP EthanolamineChEBI
Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) esterChEBI
Cytidine diphosphate ethanolamineChEBI
Cytidine 5'-(trihydrogen diphosphoric acid), p'-(2-aminoethyl) esterGenerator
Cytidine diphosphoric acid ethanolamineGenerator
CDPethanolamineHMDB
CDP Ethanolamine, p'-(32)P-labeledMeSH
Chemical FormulaC11H20N4O11P2
Average Molecular Weight446.2442
Monoisotopic Molecular Weight446.060380526
IUPAC Name[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](2-aminoethoxy)phosphinic acid
Traditional Namecdp ethanolamine
CAS Registry Number3036-18-8
SMILES
NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O
InChI Identifier
InChI=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
InChI KeyWVIMUEUQJFPNDK-PEBGCTIMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cdp-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5'-diphosphate moiety attached to the oxygen.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
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
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP-1.7ALOGPS
logP-5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area236.69 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity88.72 m³·mol⁻¹ChemAxon
Polarizability36.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6793400000-ac76da0c6087752db3c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00pj-8972160000-fd358ed61430e64ed4e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5910100000-2a4aae3a59f3f928bc14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-7900000000-70f4dc43398ae42bd718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9700000000-2d6893ab115d449880c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gvk-1512900000-bd91f3bd3454ae8dc4daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0n4i-6942200000-8c75516485feb49d2fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5900000000-624299483014ca3a86f4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Intestine
Pathways
NameSMPDB/PathwhizKEGG
Phosphatidylcholine BiosynthesisPw015076Pw015076 greyscalePw015076 simpleNot Available
Phosphatidylcholine Biosynthesis PC(11D3/11D3)Pw031122Pw031122 greyscalePw031122 simpleNot Available
Phosphatidylcholine Biosynthesis PC(11D3/11D5)Pw031124Pw031124 greyscalePw031124 simpleNot Available
Phosphatidylcholine Biosynthesis PC(11D3/11M3)Pw031128Pw031128 greyscalePw031128 simpleNot Available
Phosphatidylcholine Biosynthesis PC(11D3/11M5)Pw031129Pw031129 greyscalePw031129 simpleNot Available
Displaying entries 1 - 5 of 1847 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022691
KNApSAcK IDNot Available
Chemspider ID110296
KEGG Compound IDC00570
BioCyc IDCDP-ETHANOLAMINE
BiGG ID35382
Wikipedia LinkNot Available
METLIN ID3538
PubChem Compound123727
PDB IDNot Available
ChEBI ID16732
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ito H, Yamamoto H, Kimura Y, Kambe H, Okochi T, Kishimoto S: Affinity chromatography of human plasma gelsolin with polyphosphate compounds on immobilized Cibacron Blue F3GA. J Chromatogr. 1990 Apr 6;526(2):397-406. [PubMed:2163407 ]
  2. Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
  3. Colonna A, Russo T, Esposito F, Salvatore F, Cimino F: Determination of pseudouridine and other nucleosides in human blood serum by high-performance liquid chromatography. Anal Biochem. 1983 Apr 1;130(1):19-26. [PubMed:6869800 ]
  4. Thorell L, Sjoberg LB, Hernell O: Nucleotides in human milk: sources and metabolism by the newborn infant. Pediatr Res. 1996 Dec;40(6):845-52. [PubMed:8947961 ]
  5. Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. [PubMed:4052062 ]
  6. Weiss GB: Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline. Life Sci. 1995;56(9):637-60. [PubMed:7869846 ]
  7. Herbert KE, Scott DL, Perrett D: Determination of cytidine deaminase activity in synovial fluid by HPLC. J Pharm Biomed Anal. 1989;7(6):737-45. [PubMed:2490776 ]
  8. Hirt A, Wagner HP: Nuclear incorporation of radioactive DNA precursors and progression of cells through S. Combined radioautographic and cytophotometric studies on normal and leukaemic bone marrow and thoracic duct lymph cells of man. Cell Tissue Kinet. 1975 Sep;8(5):455-66. [PubMed:1058744 ]
  9. Parsons NJ, Ashton PR, Constantinidou C, Cole JA, Smith H: Identification by mass spectrometry of CMP-NANA in diffusible material released from high M(r) blood cell fractions that confers serum resistance on gonococci. Microb Pathog. 1993 Apr;14(4):329-35. [PubMed:8326856 ]
  10. Pery P, Luffau G, Charley J, Petit A, Rouze P, Bernard S: Cytidine-5'-diphospho-choline conjugates. II.--Immunogenicity in rats. Ann Immunol (Paris). 1979 Jul-Aug;130C(4):531-40. [PubMed:496401 ]
  11. Goldner M, Emond JP, Germani E, Launay JM, Dublanchet A: [Kinetics of sialylation of Neisseria gonorrhoeae by radiolabelled cytidine 5'monophospho-N-acetyl neuraminic acid]. Pathol Biol (Paris). 1996 Apr;44(4):249-53. [PubMed:8763586 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
Gene Name:
PCYT2
Uniprot ID:
Q99447
Molecular weight:
35199.52
Reactions
Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolaminedetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.
Gene Name:
CEPT1
Uniprot ID:
Q9Y6K0
Molecular weight:
46553.135
Reactions
CDP-Ethanolamine + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylethanolaminedetails
CDP-Ethanolamine + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylethanolaminedetails
CDP-Ethanolamine + 1-Alkyl-2-acylglycerol → Cytidine monophosphate + 1-Alkyl-2-acylglycerophosphoethanolaminedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Cytidine monophosphate → 1-Alkenyl-2-acylglycerol + CDP-Ethanolaminedetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the formation of phosphatidylethanolamine via 'Kennedy' pathway.
Gene Name:
EPT1
Uniprot ID:
Q9C0D9
Molecular weight:
45228.42
Reactions
CDP-Ethanolamine + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylethanolaminedetails
CDP-Ethanolamine + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylethanolaminedetails
CDP-Ethanolamine + 1-Alkyl-2-acylglycerol → Cytidine monophosphate + 1-Alkyl-2-acylglycerophosphoethanolaminedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Cytidine monophosphate → 1-Alkenyl-2-acylglycerol + CDP-Ethanolaminedetails