Human Metabolome Database: Showing metabocard for LysoPC(18:2(9Z,12Z)) (HMDB0010386)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (25) Show 25 proteins XML

enzymes (25) Show 25 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2008-09-16 13:20:00 UTC

Update Date

2019-07-23 05:54:30 UTC

HMDB ID

HMDB0010386

Secondary Accession Numbers

HMDB0061692
HMDB10386
HMDB61692

Metabolite Identification

Common Name

LysoPC(18:2(9Z,12Z))

Description

LysoPC(18:2(9Z,12Z)) 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(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholine	ChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholine	ChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
1-18:2-LysoPC	ChEBI
1-Linoleoyl-glycero-3-phosphocholine	ChEBI
1-Linoleoyl-GPC	ChEBI
1-Linoleoyl-GPC (18:2)	ChEBI
1-Linoleoylglycerophosphocholine	ChEBI
GPC(18:2)	ChEBI
GPC(18:2/0:0)	ChEBI
LPC 18:2(9Z,12Z)/0:0	ChEBI
LPC(18:2)	ChEBI
LPC(18:2/0:0)	ChEBI
LPC(18:2n6/0:0)	ChEBI
LPC(18:2Omega6/0:0)	ChEBI
LyPC(18:2)	ChEBI
LyPC(18:2n6/0:0)	ChEBI
LyPC(18:2omega6/0:0)	ChEBI
LysoPC 18:2(9Z,12Z)/0:0	ChEBI
LysoPC(18:2(9Z,12Z)/0:0)	ChEBI
LysoPC(18:2)	ChEBI
LysoPC(18:2/0:0)	ChEBI
LysoPC(18:2n6/0:0)	ChEBI
LysoPC(18:2omega6/0:0)	ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)	ChEBI
Lysophosphatidylcholine(18:2)	ChEBI
Lysophosphatidylcholine(18:2/0:0)	ChEBI
Lysophosphatidylcholine(18:2n6/0:0)	ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)	ChEBI
PC 18:2(9Z,12Z)/0:0	ChEBI
PC(18:2(9Z,12Z)/0:0)	ChEBI
LyPC(18:2/0:0)	HMDB
LysoPC(18:2(9Z,12Z))	Lipid Annotator
1-Linoleoyl lysolecithin	HMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholine	HMDB
1-Linoleoylglycerol-3-phosphorylcholine	HMDB
1-Linoleoylphosphatidylcholine	HMDB
Linoleoyllysolecithin	HMDB
Linoleyl lysophosphatidylcholine	HMDB
Lysophosphatidylcholine 18:2	HMDB

Chemical Formula

C₂₆H₅₀NO₇P

Average Molecular Weight

519.6515

Monoisotopic Molecular Weight

519.332489471

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

22252-07-9

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C26H50NO7P/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/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1

InChI Key

SPJFYYJXNPEZDW-FTJOPAKQSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-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 Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:28733 )
lysophosphatidylcholine 18:2 (CHEBI:28733 )
Monoacylglycerophosphocholines (LMGP01050035 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.00026 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.36	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	153.71 m³·mol⁻¹	ChemAxon
Polarizability	58.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03kl-9431010000-c20360afbdedc9d9232f	JSpectraViewer \| MoNA

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	30.33 +/- 10.3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Normal	22800120	details
Blood	Detected and Quantified	52.75 +/- 6.48 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	7.00-59.0 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	52.755 +/- 6.478 uM	Adult (>18 years old)	Both	Normal	18953024	details
Blood	Detected and Quantified	9.17 (7.36-11) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	37.27(10.8) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	26.6 +/- 9.20 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	24.9 (19.7-33.1) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	36.37 +/- 11.44 uM	Children (1-13 years old)	Both	Normal	23108202	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected and Quantified	3 +/- 3.15 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	4.15 +/- 5.33 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.0072 +/- 0.0043 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Schizophrenia	22800120	details
Blood	Detected and Quantified	21.7 +/- 7.7 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	20.0 +/- 9.5 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	19.6 +/- 8.2 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	20.6 +/- 7.5 uM	Children (1-13 years old)	Both	Obese	24740590	details
Blood	Detected and Quantified	28.23(8.39) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	31.52(11.38) uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	26010610	details
Blood	Detected and Quantified	17.582 (17.132) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	18.09 +/- 5.07 uM	Children (1-13 years old)	Both	Obese	23108202	details
Blood	Detected and Quantified	36.345 (14.315) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Urine	Detected and Quantified	0.0055 +/- 0.0028 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.0065 +/- 0.0083 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Schizophrenia
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 ]
Pregnancy
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 ]
Obesity
Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ] Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
Cirrhosis
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 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

181500 (Schizophrenia)
601665 (Obesity)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027537

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-8347

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11005824

PDB ID

Not Available

ChEBI ID

28733

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acyl-protein thioesterase 1

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

Enzyme Details

2. Group XV phospholipase A2

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

Enzyme Details

3. Calcium-dependent phospholipase A2

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

Enzyme Details

4. Group IIF secretory phospholipase A2

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

Enzyme Details

5. Cytosolic phospholipase A2

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

Enzyme Details

6. Phospholipase A2

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

Enzyme Details

7. Group XIIB secretory phospholipase A2-like protein

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

Enzyme Details

8. Group 10 secretory phospholipase A2

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

Enzyme Details

9. Group IIE secretory phospholipase A2

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

Enzyme Details

10. Acyl-protein thioesterase 2

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.

Show all enzymes and transporters

Showing metabocard for LysoPC(18:2(9Z,12Z)) (HMDB0010386)

Structure for HMDB0010386 (LysoPC(18:2(9Z,12Z)))

Enzymes