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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 13:19:58 UTC
Update Date2018-05-20 18:49:24 UTC
HMDB IDHMDB0010384
Secondary Accession Numbers
  • HMDB10384
Metabolite Identification
Common NameLysoPC(18:0)
DescriptionLysoPC(18:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:0), in particular, consists of one chain of stearic acid at the C-1 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-O-Stearoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecanoyl-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-glycero-3-phosphocholineChEBI
18:0 lyso-PCChEBI
LPC 18:0/0:0ChEBI
LPC(18:0)ChEBI
LPC(18:0/0:0)ChEBI
LysoPC 18:0/0:0ChEBI
LysoPC(18:0/0:0)ChEBI
Lysophosphatidylcholine(18:0)ChEBI
Lysophosphatidylcholine(18:0/0:0)ChEBI
PC 18:0/0:0ChEBI
PC(18:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
LyPC(18:0)HMDB
LyPC(18:0/0:0)HMDB
LysoPC a C18:0HMDB
Stearoyl alpha-lysolecithinMeSH
StearoyllysophosphatidylcholineMeSH
1-Octadecyl-glycero-3-phosphocholineMeSH
1-Stearoyl-sn-glycero-3-phosphorylcholineMeSH
Stearoyl L-alpha-lysolecithinMeSH
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholineMeSH
Stearoyl alpha-lysolecithin, (+-)-isomerMeSH
Stearoyl alpha-lysolecithin, (R)-isomerMeSH
LysoPC(18:0)Lipid Annotator
1-octadecanoyl-glycero-3-phosphocholineLipid Annotator
Chemical FormulaC26H54NO7P
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
IUPAC Name(2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name1-octadecanoyllysolecithin
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1
InChI KeyIHNKQIMGVNPMTC-RUZDIDTESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00023 g/LALOGPS
logP2.53ALOGPS
logP2.08ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.48 m³·mol⁻¹ChemAxon
Polarizability61.69 ųChemAxon
Number of Rings0ChemAxon
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 (1 TMS) - 70eV, Positivesplash10-024u-9321010000-7c4db1d8f50345253e5eView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified48.5 +/- 20.2 uMAdult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected and Quantified47.54 +/- 8.38 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified9.10-54.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified47.536 +/- 8.381 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified14.4 (12-17.7) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected and Quantified26.22(5.93) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified21.8 +/- 4.97 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified24.5 (18.5-31.9) uMInfant (0-1 year old)Not Available
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.069 +/- 0.019 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected and Quantified3.29 +/- 2.64 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified3.28 +/- 3.9 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.108 +/- 0.018 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified5.02 +/- 0.24 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.0040 (0.0013 - 0.0100) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0248 +/- 0.0131 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified21.6(5.06) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified19.323 (17.977) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified36.487 (11.673) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not Quantified Adult (>18 years old)Not SpecifiedLiver cirrhosis details
FecesDetected but not Quantified Adult (>18 years old)Not Specifiedhepatocellular carcinoma details
FecesDetected but not Quantified Adult (>18 years old)Bothliver cirrhosis details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
UrineDetected and Quantified6.07 +/- 0.35 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
UrineDetected and Quantified0.0202 +/- 0.0112 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0259 +/- 0.0362 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Cirrhosis
  1. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
  2. Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
  2. Oresic M, Seppanen-Laakso T, Sun D, Tang J, Therman S, Viehman R, Mustonen U, van Erp TG, Hyotylainen T, Thompson P, Toga AW, Huttunen MO, Suvisaari J, Kaprio J, Lonnqvist J, Cannon TD: Phospholipids and insulin resistance in psychosis: a lipidomics study of twin pairs discordant for schizophrenia. Genome Med. 2012 Jan 18;4(1):1. doi: 10.1186/gm300. [PubMed:22257447 ]
Hepatocellular carcinoma
  1. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027535
KNApSAcK IDNot Available
Chemspider ID435389
KEGG Compound IDC04230
BioCyc IDCPD-8345
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound497299
PDB IDNot Available
ChEBI ID73858
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 25 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Only showing the first 10 proteins. There are 25 proteins in total.