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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:58:58 UTC
HMDB IDHMDB0001564
Secondary Accession Numbers
  • HMDB01564
Metabolite Identification
Common NameCDP-ethanolamine
DescriptionCDP-ethanolamine, also known as cytidine 5’-diphosphoethanolamine, 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 is a very strong basic compound (based on its pKa). In humans, CDP-ethanolamine is involved in phosphatidylethanolamine biosynthesis. Outside of the human body, CDP-ethanolamine has been detected, but not quantified in, several different foods, such as Chinese water chestnuts, buffalo currants, red huckleberries, eggplants, and brazil nuts. This could make CDP-ethanolamine a potential biomarker for the consumption of these foods.
Structure
Data?1594315197
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-labeledHMDB
Cytidine 5'-diphosphate ethanolamineHMDB
Cytidine 5'-diphosphoethanolamineHMDB
Cytidine 5’-diphosphate ethanolamineHMDB
Cytidine 5’-diphosphoethanolamineHMDB
Cytidine diphosphoethanolamineHMDB
CDP-ethanolamineHMDB
Chemical FormulaC11H20N4O11P2
Average Molecular Weight446.2442
Monoisotopic Molecular Weight446.060380526
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 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
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available187.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00002086
DarkChem[M+H]+PredictedNot Available201.56331661259
DarkChem[M-H]-PredictedNot Available195.12131661259
AllCCS[M+H]+PredictedNot Available190.56932859911
AllCCS[M-H]-PredictedNot Available186.61232859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
CDP-ethanolamine,1TMS,#13670.741https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TMS,#23667.067https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TMS,#33720.0361https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TMS,#43715.6838https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TMS,#53753.1287https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TMS,#63726.6372https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#13552.5813https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#23608.8652https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#33614.8232https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#43615.1836https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#53645.6123https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#63612.5918https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#73617.338https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#83619.489https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#93642.0635https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#103649.109https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#113687.501https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#123707.1394https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#133701.8442https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#143681.3518https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#153734.3306https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#163881.5637https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TMS,#173680.2393https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#13903.7825https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#23902.9758https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#33954.1772https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#43948.6628https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#54011.0254https://arxiv.org/abs/1905.12712
CDP-ethanolamine,1TBDMS,#64007.0088https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#14018.5303https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#24050.4663https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#34058.7783https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#44101.6035https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#54127.0586https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#64051.1108https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#74056.9849https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#84098.5234https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#94123.288https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#104081.7554https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#114140.31https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#124172.382https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#134166.944https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#144134.9453https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#154248.0483https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#164250.6216https://arxiv.org/abs/1905.12712
CDP-ethanolamine,2TBDMS,#174083.0022https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6793400000-ac76da0c6087752db3c92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00pj-8972160000-fd358ed61430e64ed4e02017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-0002-0000900000-0b86b2b2cfc17d95ff902020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-0002-1012900000-c5804a13d813a5377b792020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-0032-8157900000-36b36bcbce04a95bf9622020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, negativesplash10-004i-9122000000-f9d8d35bd43030c78e8b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 35V, negativesplash10-004i-9100000000-8db373393648433147a02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-004i-9100000000-1cb47f991b97749fba0b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, negativesplash10-004i-9000000000-4a5fcad27ccf2ff239572020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, negativesplash10-004i-9000000000-6b08787f67155728185f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-001i-0029000000-1668461b10d942d91cf92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-004i-9300000000-8eef8ed8fdaa72ae58a82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-03fr-1390000000-88ee14c068713b4ad5432020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-00di-0290000000-3006b045a5e65ff5fa522020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, negativesplash10-0a4i-0900000000-4a998d56bcc8853cc4ae2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-0002-3012900000-be071eccb640152406442020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-004i-9124300000-5d5dc9798e172dc0a1e02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 78V, negativesplash10-004i-9100000000-c769c60b7993983641f02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 92V, negativesplash10-004i-9100000000-1837fdf24962abbe68052020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-001i-0009000000-0d7a52eebf0db4a36d242020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-001i-2129000000-a4a5a49c30ed6207c3332020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5910100000-2a4aae3a59f3f928bc142016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-7900000000-70f4dc43398ae42bd7182016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9700000000-2d6893ab115d449880c32016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gvk-1512900000-bd91f3bd3454ae8dc4da2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0n4i-6942200000-8c75516485feb49d2fa12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5900000000-624299483014ca3a86f42016-09-12View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
  • Placenta
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 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
Food Biomarker OntologyNot Available
VMH IDCDPEA
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  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. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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