Human Metabolome Database: Showing metabocard for LysoPC(18:1(9Z)) (HMDB02815)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (26) Show 26 proteins XML

enzymes (26) Show 26 proteins

Record Information

Version

3.6

Creation Date

2006-05-22 15:12:12 UTC

Update Date

2016-02-11 01:05:48 UTC

HMDB ID

HMDB02815

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(18:1(9Z))

Description

LysoPC(18:1(9Z)) 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(18:19Z)), in particular, consists of one chain of oleic acid at the C-1 position. The oleic acid moiety, an omega-9 fatty acid, is derived from various animal and vegetable sources such as olive oil, acai and grapeseed 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine	ChEBI
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine	ChEBI
1-Oleoyl-sn-glycero-3-phosphorylcholine	ChEBI
1-Oleoylglycerophosphocholine	ChEBI
3-Oleoyl-rac-glycerol-1-phosphorylcholine	ChEBI
LPC 18:1(9Z)/0:0	ChEBI
LPC(18:1(9Z)/0:0)	ChEBI
LysoPC 18:1(9Z)/0:0	ChEBI
LysoPC(18:1(9Z)/0:0)	ChEBI
Lysophosphatidylcholine(18:1(9Z)/0:0)	ChEBI
PC 18:1(9Z)/0:0	ChEBI
PC(18:1(9Z)/0:0)	ChEBI
1-Oleoyl-sn-glycero-3-phosphocholine	HMDB
Choline phosphate (ester) 3-ester with 1-monoolein	HMDB
Choline phosphate 3-ester with 1-monoolein	HMDB
gpcho(18:1(9Z)/0:0)[rac]	HMDB
LPC(18:1n9/0:0)	HMDB
LPC(18:1W9/0:0)	HMDB
LyPC(18:1)	HMDB
LyPC(18:1/0:0)	HMDB
LyPC(18:1W9/0:0)	HMDB
LysoPC a C18:1	HMDB
LysoPC(18:1)	HMDB
LysoPC(18:1n9/0:0)	HMDB
LysoPC(18:1W9/0:0)	HMDB
Lysophosphatidylcholine(18:1)	HMDB
Lysophosphatidylcholine(18:1/0:0)	HMDB
Lysophosphatidylcholine(18:1n9/0:0)	HMDB
Lysophosphatidylcholine(18:1W9/0:0)	HMDB
LysoPIC(18:1/0:0)	HMDB
Olein-1-mono-3-phosphate ester with choline	HMDB
Oleoyl lysolecithin	HMDB
Oleoyl lysophosphatidylcholine	HMDB

Chemical Formula

C₂₆H₅₂NO₇P

Average Molecular Weight

521.6673

Monoisotopic Molecular Weight

521.348139535

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

3542-29-8

SMILES

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

InChI Identifier

InChI=1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

InChI Key

InChIKey=YAMUFBLWGFFICM-PTGWMXDISA-N

Chemical Taxonomy

Description

This 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.

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
Dialkyl phosphate
Fatty acid ester
Choline
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oleoyl-sn-glycero-3-phosphocholine (CHEBI:74342 )
Monoacylglycerophosphocholines (LMGP01050032 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Food

Biofunction

Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane component
Membrane integrity/stability

Application

Nutrients
Stabilizers
Surfactants and Emulsifiers

Cellular locations

Extracellular
Membrane

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	0.000276 mg/mL	ALOGPS
logP	2.38	ALOGPS
logP	1.72	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	25	ChemAxon
Refractivity	152.59 m³·mol^-1	ChemAxon
Polarizability	60.01 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

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Blood

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	31.5 +/- 10.4 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	37.47 +/- 7.73 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	37.465 +/- 7.733 uM	Adult (>18 years old)	Both	Normal	18953024	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB023066

KNApSAcK ID

Not Available

Chemspider ID

17240641

KEGG Compound ID

C04230

BioCyc ID

PHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Chung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Frasch SC, Zemski-Berry K, Murphy RC, Borregaard N, Henson PM, Bratton DL: Lysophospholipids of different classes mobilize neutrophil secretory vesicles and induce redundant signaling through G2A. J Immunol. 2007 May 15;178(10):6540-8. [17475884 ]
Yang J, Zhao X, Liu X, Wang C, Gao P, Wang J, Li L, Gu J, Yang S, Xu G: High performance liquid chromatography-mass spectrometry for metabonomics: potential biomarkers for acute deterioration of liver function in chronic hepatitis B. J Proteome Res. 2006 Mar;5(3):554-61. [16512670 ]

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

Enzyme Details

11. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

Enzyme Details

12. Phosphatidylcholine-sterol acyltransferase

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:: LCAT
Uniprot ID:: P04180
Molecular weight:: 49577.545

Enzyme Details

13. Eosinophil lysophospholipase

General function:: Involved in sugar binding
Specific function:: May have both lysophospholipase and carbohydrate-binding activities.
Gene Name:: CLC
Uniprot ID:: Q05315
Molecular weight:: 16452.785

Enzyme Details

14. Group IID 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. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:: PLA2G2D
Uniprot ID:: Q9UNK4
Molecular weight:: 16546.1

Enzyme Details

15. Platelet-activating factor acetylhydrolase

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Modulates the action of platelet-activating factor (PAF) by hydrolyzing the sn-2 ester bond to yield the biologically inactive lyso-PAF. Has a specificity for substrates with a short residue at the sn-2 position. It is inactive against long-chain phospholipids.
Gene Name:: PLA2G7
Uniprot ID:: Q13093
Molecular weight:: 50076.99

Enzyme Details

16. Platelet-activating factor acetylhydrolase IB subunit gamma

General function:: Involved in hydrolase activity
Specific function:: Inactivates paf by removing the acetyl group at the sn-2 position. This is a catalytic subunit. Plays an important role during the development of brain.
Gene Name:: PAFAH1B3
Uniprot ID:: Q15102
Molecular weight:: 25734.13

Enzyme Details

17. Platelet-activating factor acetylhydrolase IB subunit beta

General function:: Involved in hydrolase activity
Specific function:: Inactivates PAF by removing the acetyl group at the sn-2 position. This is a catalytic subunit.
Gene Name:: PAFAH1B2
Uniprot ID:: P68402
Molecular weight:: 22733.715

Enzyme Details

18. Group 3 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. Shows an 11-fold preference for phosphatidylglycerol over phosphatidylcholine (PC). Preferential cleavage: 1-palmitoyl-2-linoleoyl-phosphatidylethanolamine (PE) > 1-palmitoyl-2-linoleoyl-PC > 1-palmitoyl-2-arachidonoyl-PC > 1-palmitoyl-2-arachidonoyl-PE. Plays a role in ciliogenesis.
Gene Name:: PLA2G3
Uniprot ID:: Q9NZ20
Molecular weight:: 57166.51

Enzyme Details

19. Platelet-activating factor acetylhydrolase 2, cytoplasmic

General function:: Involved in 1-alkyl-2-acetylglycerophosphocholine esterase activity
Specific function:: Has a marked selectivity for phospholipids with short acyl chains at the sn-2 position. May share a common physiologic function with the plasma-type enzyme.
Gene Name:: PAFAH2
Uniprot ID:: Q99487
Molecular weight:: 44035.255

Enzyme Details

20. 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

Enzyme Details

21. Lysophospholipid acyltransferase 5

General function:: Involved in 1-acylglycerophosphocholine O-acyltransfera
Specific function:: Acyltransferase which mediates the conversion of lysophosphatidylcholine (1-acyl-sn-glycero-3-phosphocholine or LPC) into phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine or PC) (LPCAT activity). Catalyzes also the conversion of lysophosphatidylserine (1-acyl-2-hydroxy-sn-glycero-3-phospho-L-serine or LPS) into phosphatidylserine (1,2-diacyl-sn-glycero-3-phospho-L-serine or PS) (LPSAT activity). Has also weak lysophosphatidylethanolamine acyltransferase activity (LPEAT activity). Favors polyunsaturated fatty acyl-CoAs as acyl donors compared to saturated fatty acyl-CoAs. Seems to be the major enzyme contributing to LPCAT activity in the liver. Lysophospholipid acyltransferases (LPLATs) catalyze the reacylation step of the phospholipid remodeling pathway also known as the Lands cycle.
Gene Name:: LPCAT3
Uniprot ID:: Q6P1A2
Molecular weight:: 56034.48

Enzyme Details

22. Lysophosphatidylcholine acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-independent. Mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl or 1-palmitoyl LPC as acyl donors and acceptors, respectively. May synthesize phosphatidylcholine in pulmonary surfactant, thereby playing a pivotal role in respiratory physiology.
Gene Name:: LPCAT1
Uniprot ID:: Q8NF37
Molecular weight:: 59150.675

Enzyme Details

23. Lysophosphatidylcholine acyltransferase 2

General function:: Involved in acyltransferase activity
Specific function:: Possesses both acyltransferase and acetyltransferase activities. Activity is calcium-dependent. Involved in platelet-activating factor (PAF) biosynthesis by catalyzing the conversion of the PAF precursor, 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) into 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF). Also converts lyso-PAF to 1-alkyl-phosphatidylcholine (PC), a major component of cell membranes and a PAF precursor. Under resting conditions, acyltransferase activity is preferred. Upon acute inflammatory stimulus, acetyltransferase activity is enhanced and PAF synthesis increases (By similarity).
Gene Name:: LPCAT2
Uniprot ID:: Q7L5N7
Molecular weight:: 60207.295

Enzyme Details

24. 60 kDa lysophospholipase

General function:: Involved in asparaginase activity
Specific function:: Exhibits lysophospholipase, transacylase, PAF acetylhydrolase and asparaginase activities.
Gene Name:: ASPG
Uniprot ID:: Q86U10
Molecular weight:: 60882.4

Enzyme Details

25. Phospholipase B1, membrane-associated

General function:: Involved in hydrolase activity
Specific function:: Membrane-associated phospholipase. Exhibits a calcium-independent broad substrate specificity including phospholipase A2/lysophospholipase activity. Preferential hydrolysis at the sn-2 position of diacylphospholipids and diacyglycerol, whereas it shows no positional specificity toward triacylglycerol. Exhibits also esterase activity toward p-nitrophenyl. May act on the brush border membrane to facilitate the absorption of digested lipids (By similarity).
Gene Name:: PLB1
Uniprot ID:: Q6P1J6
Molecular weight:: 161711.9

Enzyme Details

26. Cytosolic phospholipase A2 beta

General function:: Involved in metabolic process
Specific function:: Calcium-dependent phospholipase A2 that selectively hydrolyzes glycerophospholipids in the sn-2 position with a preference for arachidonoyl phospholipids. Has a much weaker activity than PLA2G4A. Isoform 3 has calcium-dependent activity against palmitoyl-arachidonyl-phosphatidylethanolamine and low level lysophospholipase activity but no activity against phosphatidylcholine. Isoform 5 does have activity against phosphatidylcholine.
Gene Name:: PLA2G4B
Uniprot ID:: P0C869
Molecular weight:: 87977.02

Showing metabocard for LysoPC(18:1(9Z)) (HMDB02815)

Structure for HMDB02815 (LysoPC(18:1(9Z)))

Enzymes