Human Metabolome Database: Showing metabocard for PC(16:0/16:0) (HMDB0000564)

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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

2005-11-16 15:48:42 UTC

Update Date

2020-02-26 21:22:20 UTC

HMDB ID

HMDB0000564

Secondary Accession Numbers

HMDB0000804
HMDB0005250
HMDB0007968
HMDB00564
HMDB00804
HMDB05250
HMDB07968

Metabolite Identification

Common Name

PC(16:0/16:0)

Description

PC(16:0/16:0) 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(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. 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
1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Dipalmitoyl-L-lecithin	ChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine	ChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine	ChEBI
1,2-Dipalmitoylphosphatidylcholine	ChEBI
1-16:0-2-16:0-Phosphatidylcholine	ChEBI
16:0-16:0-PC	ChEBI
Colfosceril palmitate	ChEBI
Colfoscerili palmitas	ChEBI
Dipalmitoyl phosphatidylcholine	ChEBI
Dipalmitoyl-GPC	ChEBI
Dipalmitoylphosphatidylcholine	ChEBI
GPC(16:0/16:0)	ChEBI
GPCho 16:0/16:0	ChEBI
GPCho(16:0/16:0)	ChEBI
Palmitate de colfosceril	ChEBI
Palmitato de colfoscerilo	ChEBI
PC 16:0/16:0	ChEBI
PC(32:0)	ChEBI
Phosphatidylcholine 16:0/16:0	ChEBI
Phosphatidylcholine(16:0/16:0)	ChEBI
Phosphatidylcholine(32:0)	ChEBI
Colfosceril palmitic acid	Generator
Palmitic acid de colfosceril	Generator
1,2-Dipalmitoyl-rac-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphocholine	HMDB
GPCho(32:0)	HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt	HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt	HMDB
1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine	HMDB
1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1,2-Dipalmitoyl-3-sn-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-3-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-a-lecithin	HMDB
1,2-Dipalmitoyl-L-a-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-alpha-lecithin	HMDB
1,2-Dipalmitoyl-L-alpha-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-L-phosphatidylcholine	HMDB
1,2-Dipalmitoyl-sn-3-glycerophosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine	HMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycerophosphocholine	HMDB
1,2-Dipalmitoyl-sn-glycerophosphorylcholine	HMDB
1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine	HMDB
1,2-Dipalmitoyl-sn-phosphatidylcholine	HMDB
1,2-Dipalmitoylglycero-3-phosphocholine	HMDB
1,2-L-a-Dipalmitoylphosphatidylcholine	HMDB
1,2-L-alpha-Dipalmitoylphosphatidylcholine	HMDB
b,g-Dipalmitoyl L-a-phosphatidylcholine	HMDB
b,g-Dipalmitoyl L-alpha-phosphatidylcholine	HMDB
b,g-Dipalmitoyl-L-(a)-lecithin	HMDB
b,g-Dipalmitoyl-L-phosphatidylcholine	HMDB
Dihexadecanoyl-sn-glycero-3-phosphocholine	HMDB
Dipalmitoyl L-a-phosphatidylcholine	HMDB
Dipalmitoyl L-alpha-phosphatidylcholine	HMDB
Dipalmitoyl-L-3-glycerylphosphorylcholine	HMDB
Dipalmitoyl-L-a-lecithin	HMDB
Dipalmitoyl-L-a-phosphatidylcholine	HMDB
Dipalmitoyl-L-alpha-lecithin	HMDB
Dipalmitoyl-L-alpha-phosphatidylcholine	HMDB
Dipalmitoyl-sn-3-phosphatidylcholine	HMDB
DPPC	HMDB
L-1,2-Dipalmitoyl-a-lecithin	HMDB
L-1,2-Dipalmitoyl-alpha-lecithin	HMDB
L-1,2-Dipalmitoylphosphatidylcholine	HMDB
L-a-1,2-Dipalmitoyl lecithin	HMDB
L-a-Dipalmitoylecithin	HMDB
L-a-Dipalmitoyllecithin	HMDB
L-a-Dipalmitoylphosphatidylcholine	HMDB
L-a-DPPC	HMDB
L-alpha-1,2-Dipalmitoyl lecithin	HMDB
L-alpha-Dipalmitoylecithin	HMDB
L-alpha-Dipalmitoyllecithin	HMDB
L-alpha-Dipalmitoylphosphatidylcholine	HMDB
L-alpha-DPPC	HMDB
L-b,g-Dipalmitoyl-a-lecithin	HMDB
L-b,g-Dipalmitoyl-a-phosphatidylcholine	HMDB
L-b,g-Dipalmitoyl-alpha-lecithin	HMDB
L-b,g-Dipalmitoyl-alpha-phosphatidylcholine	HMDB
L-b,g-Dipalmitoylphosphatidylcholine	HMDB
L-Dipalmitoyl lecithin	HMDB
L-DPPC	HMDB
PC Aa C32:0	HMDB
sn-3-Dipalmitoyllecithin	HMDB
PC(16:0/16:0)	Lipid Annotator
1,2-Dipalmitoyl-GPC	HMDB

Chemical Formula

C₄₀H₈₀NO₈P

Average Molecular Weight

734.0389

Monoisotopic Molecular Weight

733.562155053

IUPAC Name

(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

63-89-8

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

InChI Key

KILNVBDSWZSGLL-KXQOOQHDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphatidylcholine 32:0 (CHEBI:72999 )
Diacylglycerophosphocholines (LMGP01010564 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical process:

Cellular process:

Cell signaling

Biochemical pathway:

Role

Biological role:

Industrial application:

Food and nutrition:

Pharmaceutical industry:

Pharmaceutical

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	2.4e-05 g/L	ALOGPS
logP	5.29	ALOGPS
logP	8.11	ChemAxon
logS	-7.5	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	215.87 m³·mol⁻¹	ChemAxon
Polarizability	92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-e904df388d2d70397c9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-18b2f9e577dc5a9bfcb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900211200-e76cb9b9e105ad69b570	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phospholipid Biosynthesis
Phosphatidylcholine Biosynthesis PC(16:0/16:0)		Not Available
Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	584.557 +/- 134.506 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	13.6 (11.8-15.7) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	13.87 (0.11-42.20) uM	Adolescent (13-18 years old)	Both	Normal	28959601	details
Blood	Detected and Quantified	8.50-30.0 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	15.3 (12.7-18.3) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	15.1 +/- 3.01 uM	Adult (>18 years old)	Both	Normal	28278231	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected and Quantified	0.198 +/- 0.349 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.0035 (0.0013-0.0071) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0038 +/- 0.0081 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 and Quantified	17.85 (12.57-49.03) uM	Adolescent (13-18 years old)	Both	Pain or fever	28959601	details
Blood	Detected and Quantified	11.830 (10.249) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	21.468 (6.561) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	20.56 (12.79-46.67) uM	Adolescent (13-18 years old)	Both	Acetaminophen overdose	28959601	details
Blood	Detected and Quantified	10.6 +/- 2.7 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	12.5 +/- 3.2 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Feces	Detected but not Quantified		Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Urine	Detected and Quantified	0.0026 +/- 0.0025 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.0035 +/- 0.0065 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	214.738 +/- 57.817 uM	Adult (>18 years old)	Both	Normal (Most Probable)	Calculated using MetaboAnalyst
Blood	584.550 +/- 134.486 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
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.
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

601665 (Obesity)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB09114

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022121

KNApSAcK ID

Not Available

Chemspider ID

398235

KEGG Compound ID

C00157

BioCyc ID

1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5548

PubChem Compound

452110

PDB ID

Not Available

ChEBI ID

72999

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Bouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 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(16:0/16:0) (HMDB0000564)

Structure for HMDB0000564 (PC(16:0/16:0))

Enzymes

Transporters