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Identification
NamePhosphocholine
Accession NumberDB03945  (EXPT02629)
TypeSmall Molecule
GroupsExperimental
Description

Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII96AN057F7A
CAS number107-73-3
WeightAverage: 184.1507
Monoisotopic: 184.073869485
Chemical FormulaC5H15NO4P
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphocholines. These are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Fabry diseaseDiseaseSMP00525
Sphingolipid MetabolismMetabolicSMP00034
Metachromatic Leukodystrophy (MLD)DiseaseSMP00347
Phospholipid BiosynthesisMetabolicSMP00025
Gaucher DiseaseDiseaseSMP00349
Globoid Cell LeukodystrophyDiseaseSMP00348
Krabbe diseaseDiseaseSMP00526
Lamivudine Metabolism PathwayDrug metabolismSMP00649
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-3d961174f1a27a76e351View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-fff62078da4bf8f84753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9000000000-275c66ca16bdb9344ee2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-1dbd5123486fc544909bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001r-4900000000-a77ea15e15088c9209feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-002r-9600000000-55422f402ca1581e8111View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0072-9100000000-80e4e45c1a0a5ef016ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-006t-9000000000-347eed4168ee48195753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0040-6900000000-8bbb64f5a93a59787a0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-9700000000-1e35f21857e363fec75aView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 phosphorylcholine. Can interact with DNA and histones and may scavenge nuclear material released from damaged circulating cells.
Gene Name:
CRP
Uniprot ID:
P02741
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23