Human Metabolome Database: Showing metabocard for PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (HMDB0008022)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (77)transporters (1) Show 78 proteins XML

enzymes (77)transporters (1) Show 78 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2008-09-12 01:30:02 UTC

Update Date

2019-01-11 19:22:08 UTC

HMDB ID

HMDB0008022

Secondary Accession Numbers

HMDB08022

Metabolite Identification

Common Name

PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))

Description

PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GPCho(38:6)	Lipid Annotator
PC(16:1/22:5)	Lipid Annotator
Phosphatidylcholine(16:1/22:5)	Lipid Annotator
Phosphatidylcholine(38:6)	Lipid Annotator
Lecithin	Lipid Annotator
GPCho(16:1/22:5)	Lipid Annotator
PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))	Lipid Annotator
1-palmitoleoyl-2-osbondoyl-sn-glycero-3-phosphocholine	Lipid Annotator
1-(9Z-hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine	Lipid Annotator
PC(38:6)	Lipid Annotator

Chemical Formula

C₄₆H₈₀NO₈P

Average Molecular Weight

806.1031

Monoisotopic Molecular Weight

805.562155053

IUPAC Name

(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16-17,19-21,23-24,27,29,33,35,44H,6-13,15,18,22,25-26,28,30-32,34,36-43H2,1-5H3/b16-14-,19-17-,21-20-,24-23-,29-27-,35-33-/t44-/m1/s1

InChI Key

WCODZEYPAWOVBI-UMQSOSPQSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

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 process:

Cellular process:

Cell signaling

Biochemical pathway:

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	3.1e-05 g/L	ALOGPS
logP	5.78	ALOGPS
logP	8.61	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	250.17 m³·mol⁻¹	ChemAxon
Polarizability	95.45 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9164311220-a2e8d028fea91f66888c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4394111100-bcd77868c37d93dcf4be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-8194003100-6806d5c054592a8c8e09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0093000030-1d9f28fbfa7b34b402f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0091000100-b23939487f6cfd97d61a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdr-5095000000-59ca2570f03fdcda5d93	View in MoNA

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	60.6 (50.1-72.9 ) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	49.1 (37.8-60.8) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	103.41(31.68) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	88.0 +/- 25.0 uM	Adult (>18 years old)	Both	Normal	28278231	details
Feces	Detected and Quantified	0.07 +/- 0.04 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.12 +/- 0.11 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.030 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.13 +/- 0.15 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details
Urine	Detected and Quantified	0.001 (0.0005-0.0036) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	51.9 +/- 20.0 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	60.5 +/- 21.7 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	85.74(28.21) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	79.2(25.38) uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	26010610	details
Blood	Detected and Quantified	90.567 (84.144) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	178.280 (54.427) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Urine	Detected and Quantified	0.78 +/- 0.08 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.027 +/- 0.010 uM	Adult (>18 years old)	Both	Normal (Most Probable)	Calculated using MetaboAnalyst
Blood	7.267 +/- 0.802 uM	Adult (>18 years old)	Both	Normal (Upper Limit)	Calculated using MetaboAnalyst

Associated Disorders and Diseases

Disease References

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
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 ] Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.

Associated OMIM IDs

601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53478685

PDB ID

Not Available

ChEBI ID

89657

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 78 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

Transporters

Enzyme Details

1. Multidrug resistance protein 3

General function:: Involved in ATP binding
Specific function:: Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:: ABCB4
Uniprot ID:: P21439
Molecular weight:: 141521.8

Only showing the first 10 proteins. There are 78 proteins in total.

Show all enzymes and transporters

Showing metabocard for PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (HMDB0008022)

Structure for HMDB0008022 (PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

Enzymes

Transporters