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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (14) Show 14 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:30 UTC

HMDB ID

HMDB0001565

Secondary Accession Numbers

HMDB0000284
HMDB00284
HMDB01565

Metabolite Identification

Common Name

Phosphorylcholine

Description

Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Choline phosphate	ChEBI
CHOP	ChEBI
N-Trimethyl-2-aminoethylphosphonate	ChEBI
O-Phosphocholine	ChEBI
Phosphoryl-choline	ChEBI
Trimethyl(2-(phosphonooxy)ethyl)ammonium	ChEBI
Phosphocholine	Kegg
Choline phosphoric acid	Generator
N-Trimethyl-2-aminoethylphosphonic acid	Generator
Chloride, phosphorylcholine	HMDB
Phosphate, choline	HMDB
Phosphorylcholine chloride	HMDB
Phosphate chloride, choline	HMDB
Chloride, choline phosphate	HMDB
Choline chloride dihydrogen phosphate	HMDB
Choline phosphate chloride	HMDB

Chemical Formula

C₅H₁₅NO₄P

Average Molecular Weight

184.1507

Monoisotopic Molecular Weight

184.073869485

IUPAC Name

[2-(trimethylazaniumyl)ethoxy]phosphonic acid

Traditional Name

ChoP

CAS Registry Number

3616-04-4

SMILES

C[N+](C)(C)CCOP(O)(O)=O

InChI Identifier

InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1

InChI Key

YHHSONZFOIEMCP-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphocholines. Phosphocholines 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

Substituents

Phosphocholine
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Tetraalkylammonium salt
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphocholines (CHEBI:18132 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Astarita_pos	135.3	30932474
[M+H]+	MetCCS_test_pos	135.9	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.36 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.07 m³·mol⁻¹	ChemAxon
Polarizability	17.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.175	31661259
DarkChem	[M-H]-	134.381	31661259
AllCCS	[M+H]+	138.837	32859911
AllCCS	[M-H]-	146.585	32859911
DeepCCS	[M+H]+	127.031	30932474
DeepCCS	[M-H]-	123.327	30932474
DeepCCS	[M-2H]-	160.738	30932474
DeepCCS	[M+Na]+	136.258	30932474
AllCCS	[M+H]+	138.8	32859911
AllCCS	[M+H-H2O]+	135.3	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	146.6	32859911
AllCCS	[M+Na-2H]-	148.5	32859911
AllCCS	[M+HCOO]-	150.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.52 minutes	32390414
Predicted by Siyang on May 30, 2022	8.3108 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	446.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	340.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	249.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	68.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	264.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	245.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	929.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	570.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	569.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	887.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	546.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	307.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphorylcholine	C[N+](C)(C)CCOP(O)(O)=O	2126.8	Standard polar	33892256
Phosphorylcholine	C[N+](C)(C)CCOP(O)(O)=O	1181.9	Standard non polar	33892256
Phosphorylcholine	C[N+](C)(C)CCOP(O)(O)=O	1473.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphorylcholine,1TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C	1441.6	Semi standard non polar	33892256
Phosphorylcholine,1TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C	1374.9	Standard non polar	33892256
Phosphorylcholine,1TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O)O[Si](C)(C)C	1792.0	Standard polar	33892256
Phosphorylcholine,2TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1466.2	Semi standard non polar	33892256
Phosphorylcholine,2TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1490.9	Standard non polar	33892256
Phosphorylcholine,2TMS,isomer #1	C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1537.0	Standard polar	33892256
Phosphorylcholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C	1667.5	Semi standard non polar	33892256
Phosphorylcholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C	1612.6	Standard non polar	33892256
Phosphorylcholine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)OCC[N+](C)(C)C	1887.7	Standard polar	33892256
Phosphorylcholine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1918.9	Semi standard non polar	33892256
Phosphorylcholine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1919.0	Standard non polar	33892256
Phosphorylcholine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1731.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphorylcholine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-cb21d52ab18bca51e777	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphorylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-3d961174f1a27a76e351	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9300000000-fff62078da4bf8f84753	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-007a-9000000000-275c66ca16bdb9344ee2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-001i-0900000000-1dbd5123486fc544909b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-001r-4900000000-a77ea15e15088c9209fe	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-002r-9600000000-55422f402ca1581e8111	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-006t-9000000000-347eed4168ee48195753	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0040-6900000000-8bbb64f5a93a59787a0d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-001i-9700000000-1e35f21857e363fec75a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF , negative-QTOF	splash10-001i-9700000000-1e35f21857e363fec75a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOF	splash10-001i-0900000000-1dbd5123486fc544909b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOF	splash10-001r-4900000000-2fd51d187f11ab05dd9f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOF	splash10-002r-9600000000-57b8ad3f9f3c91e92bdf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOF	splash10-0072-9100000000-80e4e45c1a0a5ef016ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QQ , positive-QTOF	splash10-006t-9000000000-347eed4168ee48195753	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine LC-ESI-QTOF , positive-QTOF	splash10-0040-6900000000-8bbb64f5a93a59787a0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine 35V, Positive-QTOF	splash10-001i-3900000000-d64b56779c67fb13738d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine 20V, Positive-QTOF	splash10-00ds-9200000000-e65557cea0495452a5be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine 35V, Positive-QTOF	splash10-001i-4900000000-4d34ff6b3e7ac6a8a67a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine 40V, Positive-QTOF	splash10-000t-9000000000-a00e7417eed2c9707fe5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phosphorylcholine 10V, Positive-QTOF	splash10-001i-2900000000-08400ca570d2f786b4db	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphorylcholine 10V, Positive-QTOF	splash10-001r-9500000000-7b0806b933e054fe2fc1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphorylcholine 20V, Positive-QTOF	splash10-001r-9200000000-8134826bf94ee033006d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphorylcholine 40V, Positive-QTOF	splash10-000i-9000000000-b75c9abd7c4ad9a57776	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Placenta
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Phospholipid Biosynthesis
Starch and sucrose metabolism	Not Available
Gaucher Disease		Not Available
Globoid Cell Leukodystrophy		Not Available
Metachromatic Leukodystrophy (MLD)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.2 +/- 1.0 uM	Adult (>18 years old)	Female	Normal	16043031	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Breast Milk	Detected and Quantified	570 +/- 136 uM	Adult (>18 years old)	Female	Normal	8839502	details
Breast Milk	Detected and Quantified	355 +/- 171 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.42 +/- 0.71 uM	Adult (>18 years old)	Not Specified	Normal	15465626	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	13.11 +/- 9.45 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	5.42 +/- 3.54 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	5.24 +/- 1.97 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	5.21 +/- 2.21 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	4.44 +/- 2.30 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	3.46 +/- 1.59 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.21 +/- 2.22 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	1.1 (0.7-3.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Lung cancer	25961003	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.32 +/- 0.38 uM	Adult (>18 years old)	Not Specified	Vascular dementia	15465626	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.16 +/- 0.84 uM	Elderly (>65 years old)	Not Specified	Alzheimer's disease	15465626	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	21799048	details

Associated Disorders and Diseases

Disease References

Lung Cancer
Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Multi-infarct dementia
Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Alzheimer's disease
Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

211980 (Lung Cancer)
104300 (Alzheimer's disease)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB03945

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18132

Food Biomarker Ontology

Not Available

VMH ID

CHOLP

MarkerDB ID

MDB00000338

Good Scents ID

Not Available

References

Synthesis Reference

Vijeeta, T.; Reddy, J. R. C.; Rao, B. V. S. K.; Karuna, M. S. L.; Prasad, R. B. N. Phospholipase-mediated preparation of 1-ricinoleoyl-2-acyl-sn- glycero-3-phosphocholine from soya and egg phosphatidylcholine. Biotechnology Letters (2004), 26(13), 1077-10

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. [PubMed:15465626 ]
Pomfret EA, daCosta KA, Schurman LL, Zeisel SH: Measurement of choline and choline metabolite concentrations using high-pressure liquid chromatography and gas chromatography-mass spectrometry. Anal Biochem. 1989 Jul;180(1):85-90. [PubMed:2817347 ]
Miller BL, Read S, Tang C, Jenden D: Differences in red blood cell choline and lipid-bound choline between patients with Alzheimer disease and control subjects. Neurobiol Aging. 1991 Jan-Feb;12(1):61-4. [PubMed:2002884 ]
Katz-Brull R, Margalit R, Degani H: Differential routing of choline in implanted breast cancer and normal organs. Magn Reson Med. 2001 Jul;46(1):31-8. [PubMed:11443708 ]
Stoll AL, Renshaw PF, De Micheli E, Wurtman R, Pillay SS, Cohen BM: Choline ingestion increases the resonance of choline-containing compounds in human brain: an in vivo proton magnetic resonance study. Biol Psychiatry. 1995 Feb 1;37(3):170-4. [PubMed:7727625 ]
Nordenstam G, Andersson B, Briles D, Brooks JW Jr, Oden A, Svanborg A, Eden CS: High anti-phosphorylcholine antibody levels and mortality associated with pneumonia. Scand J Infect Dis. 1990;22(2):187-95. [PubMed:2356441 ]
Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. [PubMed:25935 ]
Toth M, Gimes G: Phosphocholine transferase is more efficient than diacylglycerol kinase as possible attenuator of diacylglycerol signals in primordial human placenta. Acta Physiol Hung. 1993;81(4):341-54. [PubMed:8067249 ]
Kanekura T, Nagata Y, Miyoshi H, Ishihara K, Nakabayashi N, Kanzaki T: Beneficial effects of synthetic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate), on stratum corneum function. Clin Exp Dermatol. 2002 May;27(3):230-4. [PubMed:12072015 ]
Ueda H, Watanabe J, Konno T, Takai M, Saito A, Ishihara K: Asymmetrically functional surface properties on biocompatible phospholipid polymer membrane for bioartificial kidney. J Biomed Mater Res A. 2006 Apr;77(1):19-27. [PubMed:16345080 ]
Kanfer JN, Pettegrew JW, Moossy J, McCartney DG: Alterations of selected enzymes of phospholipid metabolism in Alzheimer's disease brain tissue as compared to non-Alzheimer's demented controls. Neurochem Res. 1993 Mar;18(3):331-4. [PubMed:8386814 ]
Hartwich J, Dembinska-Kiec A, Gruca A, Motyka M, Partyka L, Skrzeczynska J, Bzowska M, Pryjma J, Huber J, Leitinger N, Schmitz G: Regulation of platelet adhesion by oxidized lipoproteins and oxidized phospholipids. Platelets. 2002 May;13(3):141-51. [PubMed:12180496 ]
Nakabayashi N, Iwasaki Y: Copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) as biomaterials. Biomed Mater Eng. 2004;14(4):345-54. [PubMed:15472384 ]
Jansen SM, Groener JE, Bax W, Suter A, Saftig P, Somerharju P, Poorthuis BJ: Biosynthesis of phosphatidylcholine from a phosphocholine precursor pool derived from the late endosomal/lysosomal degradation of sphingomyelin. J Biol Chem. 2001 Jun 1;276(22):18722-7. Epub 2001 Mar 16. [PubMed:11376003 ]
Iwasaki Y, Yamasaki A, Ishihara K: Platelet compatible blood filtration fabrics using a phosphorylcholine polymer having high surface mobility. Biomaterials. 2003 Sep;24(20):3599-604. [PubMed:12809789 ]
Tomassen SF, Fekkes D, de Jonge HR, Tilly BC: Osmotic swelling-provoked release of organic osmolytes in human intestinal epithelial cells. Am J Physiol Cell Physiol. 2004 Jun;286(6):C1417-22. Epub 2004 Feb 11. [PubMed:14960416 ]
Dagnelie PC, Bell JD, Cox IJ, Menon DK, Sargentoni J, Coutts GA, Williams SC: Effects of fish oil on phospholipid metabolism in human and rat liver studied by 31P NMR spectroscopy in vivo and in vitro. NMR Biomed. 1993 Mar-Apr;6(2):157-62. [PubMed:8499247 ]
Bell JD, Cox IJ, Sargentoni J, Peden CJ, Menon DK, Foster CS, Watanapa P, Iles RA, Urenjak J: A 31P and 1H-NMR investigation in vitro of normal and abnormal human liver. Biochim Biophys Acta. 1993 Nov 25;1225(1):71-7. [PubMed:8241291 ]
Zhu X, Song J, Mar MH, Edwards LJ, Zeisel SH: Phosphatidylethanolamine N-methyltransferase (PEMT) knockout mice have hepatic steatosis and abnormal hepatic choline metabolite concentrations despite ingesting a recommended dietary intake of choline. Biochem J. 2003 Mar 15;370(Pt 3):987-93. [PubMed:12466019 ]
Planchart S, Botto C, Alarcon de Noya B, Bonifacino R, Vivas L, Spencer L, Vivas S: Evaluation of the double diffusion, enzyme immunoassay and immunoblotting techniques, for the diagnosis of human hydatid disease in tropical areas. Rev Inst Med Trop Sao Paulo. 1994 May-Jun;36(3):205-10. [PubMed:7855483 ]
Lochnit G, Dennis RD, Geyer R: Phosphorylcholine substituents in nematodes: structures, occurrence and biological implications. Biol Chem. 2000 Sep-Oct;381(9-10):839-47. [PubMed:11076016 ]
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 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Choline-phosphate cytidylyltransferase B

General function:: Involved in catalytic activity
Specific function:: Controls phosphatidylcholine synthesis.
Gene Name:: PCYT1B
Uniprot ID:: Q9Y5K3
Molecular weight:: 40228.99

Reactions

Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicoline	details
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonate	details

Enzyme Details

2. Choline-phosphate cytidylyltransferase A

General function:: Involved in catalytic activity
Specific function:: Controls phosphatidylcholine synthesis.
Gene Name:: PCYT1A
Uniprot ID:: P49585
Molecular weight:: 41730.67

Reactions

Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicoline	details
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + CMP-N-trimethyl-2-aminoethylphosphonate	details

Enzyme Details

3. Sphingomyelin phosphodiesterase

General function:: Involved in hydrolase activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:: SMPD1
Uniprot ID:: P17405
Molecular weight:: 69935.53

Reactions

Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholine	details
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholine	details

Enzyme Details

4. Choline/ethanolamine kinase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:: CHKB
Uniprot ID:: Q9Y259
Molecular weight:: 45270.99

Reactions

Adenosine triphosphate + Choline → ADP + Phosphorylcholine	details

Enzyme Details

5. Choline kinase alpha

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:: CHKA
Uniprot ID:: P35790
Molecular weight:: 52248.53

Reactions

Adenosine triphosphate + Choline → ADP + Phosphorylcholine	details

Enzyme Details

6. Ectonucleotide pyrophosphatase/phosphodiesterase family member 7

General function:: Involved in catalytic activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:: ENPP7
Uniprot ID:: Q6UWV6
Molecular weight:: 51493.415

Reactions

Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholine	details
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholine	details

Enzyme Details

7. Sphingomyelin phosphodiesterase 2

General function:: Involved in metal ion binding
Specific function:: Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:: SMPD2
Uniprot ID:: O60906
Molecular weight:: 47645.29

Reactions

Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholine	details
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholine	details

Enzyme Details

8. C-reactive protein

General function:: Involved in choline 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:: 25038.4

Enzyme Details

9. Phosphoethanolamine/phosphocholine phosphatase

General function:: Involved in phosphatase activity
Specific function:: Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:: PHOSPHO1
Uniprot ID:: Q8TCT1
Molecular weight:: 32350.505

Reactions

Phosphorylcholine + Water → Choline + Phosphate	details

Enzyme Details

10. Sphingomyelin phosphodiesterase 3

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:: SMPD3
Uniprot ID:: Q9NY59
Molecular weight:: 71080.1

Reactions

Sphingomyelin + Water → N-acylsphingosine + Phosphorylcholine	details
Sphingomyelin + Water → N-Acylsphingosine + Phosphorylcholine	details

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Phosphorylcholine (HMDB0001565)

MOL for HMDB0001565 (Phosphorylcholine)

3D MOL for HMDB0001565 (Phosphorylcholine)

3D SDF for HMDB0001565 (Phosphorylcholine)

3D-SDF for HMDB0001565 (Phosphorylcholine)

PDB for HMDB0001565 (Phosphorylcholine)

3D PDB for HMDB0001565 (Phosphorylcholine)

SMILES for HMDB0001565 (Phosphorylcholine)

INCHI for HMDB0001565 (Phosphorylcholine)

Structure for HMDB0001565 (Phosphorylcholine)

3D Structure for HMDB0001565 (Phosphorylcholine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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