N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium

Identification

Name
N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium
Accession Number
DB03945  (EXPT02629)
Type
Small Molecule
Groups
Experimental
Description

Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.

Structure
Thumb
Synonyms
  • Choline, dihydrogen phosphate (ester) (8CI)
  • Ethanaminium, N,N,N-trimethyl-2-(phosphonooxy)-
  • Phosphocholine cation
Product Ingredients
IngredientUNIICASInChI Key
Phosphorylcholine chloride96AN057F7A107-73-3PYJNAPOPMIJKJZ-UHFFFAOYSA-N
Categories
UNII
Not Available
CAS number
3616-04-4
Weight
Average: 184.1507
Monoisotopic: 184.073869485
Chemical Formula
C5H15NO4P
InChI Key
YHHSONZFOIEMCP-UHFFFAOYSA-O
InChI
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
IUPAC Name
[2-(trimethylazaniumyl)ethoxy]phosphonic acid
SMILES
C[N+](C)(C)CCOP(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UC-reactive proteinNot AvailableHuman
UEpididymal sperm-binding protein 1Not AvailableHuman
UGamma-hemolysin component BNot AvailableStaphylococcus aureus (strain MW2)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Metachromatic Leukodystrophy (MLD)Disease
Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(15:0/15:0)Metabolic
Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(15:0/24:0)Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/14:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/14:0)Metabolic
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))Metabolic
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:0/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:0/18:0)Metabolic
Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:0/24:0)Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/16:0)Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcemetacinThe therapeutic efficacy of Acemetacin can be decreased when used in combination with N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium.Approved, Experimental, Investigational
Calcium carbimideThe risk or severity of adverse effects can be increased when Calcium carbimide is combined with N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium.Withdrawn
LacidipineN,N,N-Trimethyl-2-(phosphonooxy)ethanaminium may increase the hypotensive activities of Lacidipine.Approved, Investigational
LorpiprazoleThe therapeutic efficacy of N,N,N-Trimethyl-2-(phosphonooxy)ethanaminium can be increased when used in combination with Lorpiprazole.Approved
Food Interactions
Not Available

References

Synthesis Reference

Louis J. Rezanka, "SYNTHESIS OF PHOSPHOCHOLINE ESTER DERIVATIVES AND CONJUGATES THEREOF." U.S. Patent US20080175852, issued July 24, 2008.

US20080175852
General References
Not Available
External Links
Human Metabolome Database
HMDB0001565
KEGG Compound
C00588
PubChem Compound
1014
PubChem Substance
46508785
ChemSpider
989
ChEBI
18132
ChEMBL
CHEMBL1235161
HET
PC
Wikipedia
Phosphocholine
PDB Entries
1b09 / 1h8p / 1o72 / 1wra / 2bib / 2ckq / 2mcp / 2x6a / 2x6b / 2x6c
show 29 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.36 mg/mLALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.07 m3·mol-1ChemAxon
Polarizability17.23 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9996
Blood Brain Barrier+0.7104
Caco-2 permeable-0.5258
P-glycoprotein substrateSubstrate0.5662
P-glycoprotein inhibitor INon-inhibitor0.949
P-glycoprotein inhibitor IINon-inhibitor0.9765
Renal organic cation transporterNon-inhibitor0.8337
CYP450 2C9 substrateNon-substrate0.7553
CYP450 2D6 substrateNon-substrate0.7684
CYP450 3A4 substrateSubstrate0.5308
CYP450 1A2 substrateNon-inhibitor0.8738
CYP450 2C9 inhibitorNon-inhibitor0.8356
CYP450 2D6 inhibitorNon-inhibitor0.9089
CYP450 2C19 inhibitorNon-inhibitor0.8238
CYP450 3A4 inhibitorNon-inhibitor0.9052
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9787
Ames testNon AMES toxic0.7789
CarcinogenicityNon-carcinogens0.5899
BiodegradationReady biodegradable0.6165
Rat acute toxicity2.6000 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6303
hERG inhibition (predictor II)Non-inhibitor0.7878
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0900000000-3d961174f1a27a76e351
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-9300000000-fff62078da4bf8f84753
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-007a-9000000000-275c66ca16bdb9344ee2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-0900000000-1dbd5123486fc544909b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001r-4900000000-a77ea15e15088c9209fe
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-002r-9600000000-55422f402ca1581e8111
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0072-9100000000-80e4e45c1a0a5ef016ce
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-006t-9000000000-347eed4168ee48195753
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0040-6900000000-8bbb64f5a93a59787a0d
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-9700000000-1e35f21857e363fec75a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-9700000000-1e35f21857e363fec75a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-1dbd5123486fc544909b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001r-4900000000-2fd51d187f11ab05dd9f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-002r-9600000000-57b8ad3f9f3c91e92bdf
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0072-9100000000-80e4e45c1a0a5ef016ce
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006t-9000000000-347eed4168ee48195753
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0040-6900000000-8bbb64f5a93a59787a0d
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phosphocholines. These are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Phosphocholines
Alternative Parents
Monoalkyl phosphates / Tetraalkylammonium salts / Organopnictogen compounds / Organooxygen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Phosphocholine / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Tetraalkylammonium salt / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphocholines (CHEBI:18132)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Low-density lipoprotein particle receptor binding
Specific Function
Displays several functions associated with host defense: it promotes agglutination, bacterial capsular swelling, phagocytosis and complement fixation through its calcium-dependent binding to phosph...
Gene Name
CRP
Uniprot ID
P02741
Uniprot Name
C-reactive protein
Molecular Weight
25038.385 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Binds to spermatozoa upon ejaculation and may play a role in sperm capacitation. Has phosphorylcholine-binding activity (By similarity).
Gene Name
ELSPBP1
Uniprot ID
Q96BH3
Uniprot Name
Epididymal sperm-binding protein 1
Molecular Weight
26106.11 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Toxin that seems to act by forming pores in the membrane of the cell. Has a hemolytic and a leucotoxic activity (By similarity).
Gene Name
hlgB
Uniprot ID
P0A076
Uniprot Name
Gamma-hemolysin component B
Molecular Weight
36710.87 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:57