ECMDB: PE(15:0cyclo/14:0(3-OH)) (ECMDB23499) (M2MDB003889)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (3)XML

Proteins (7)

Record Information

Version

2.0

Creation Date

2012-10-24 09:54:28 -0600

Update Date

2015-09-14 11:19:52 -0600

Secondary Accession Numbers

ECMDB23499

Identification

Name:

PE(15:0cyclo/14:0(3-OH))

Description

PE(15:0cyclo/14:0(3-OH)) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(15:0cyclo/14:0(3-OH)), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to the C-1 atom, and one 3-hydroxytetradecanoyl to the C-2 atom. 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. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-(cis-9,10-Methylenetetradecanoyl)-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoethanolamine
1-(cis-9,10-Methylenetetradecanoyl)-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoethanolamine
GPEtn(15:0/14:0)
GPEtn(29:0)
PE(15:0/14:0)
PE(29:0)
Phophatidylethanolamine(15:0/14:0)
Phophatidylethanolamine(29:0)

Chemical Formula:

C₃₄H₆₆NO₉P

Weight:

Average: 663.8629
Monoisotopic: 663.447519227

InChI Key:

LOGAHLCRICZMSC-KIHBOBKYSA-N

InChI:

InChI=1S/C34H66NO9P/c1-3-5-7-8-9-10-11-14-17-21-31(36)26-34(38)44-32(28-43-45(39,40)42-24-23-35)27-41-33(37)22-18-15-12-13-16-20-30-25-29(30)19-6-4-2/h29-32,36H,3-28,35H2,1-2H3,(H,39,40)/t29?,30?,31?,32-/m1/s1

CAS number:

Not Available

IUPAC Name:

(2-aminoethoxy)[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid

Traditional IUPAC Name:

2-aminoethoxy((2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid

SMILES:

CCCCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(O)(=O)OCCN

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Substituents

Diacylglycero-3-phosphoethanolamine
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.06	ALOGPS
logP	7.11	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	154.61 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	176.81 m³·mol⁻¹	ChemAxon
Polarizability	78.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

SMPDB Pathways:

phospholipid biosynthesis CL(15:0cyclo/14:0/16:1(9Z)/16:1(9Z))	PW001054
phospholipid biosynthesis CL(15:0cyclo/14:0/19:0cycv8c/19:0cycv8c)	PW001058
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/16:0)	PW001059
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/16:1(9Z))	PW001060
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/14:0)	PW001066
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/14:0)	PW001071
phospholipid biosynthesis CL(15:0cyclo/16:0/14:0/15:0cyclo)	PW001094
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/14:0)	PW001095
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/14:0/15:0cyclo)	PW001117
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/14:0/16:1(9Z))	PW001118
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/14:0)	PW001119
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/14:0)	PW001126
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/14:0/18:1(9Z))	PW001160
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/14:0/19:0cycv8c)	PW001183
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/14:0)	PW001198
phospholipid biosynthesis CL(16:0/15:0cyclo/14:0/15:0cyclo)	PW001220
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/14:0)	PW001221
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/15:0cyclo)	PW001511

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9140202000-c4ba092ffae21307772f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9230101000-4af9a6ecc2e7c7b4fffe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9440000000-cac92b28be6e123d91d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-0290204000-9cd44b50f604ebd2c8dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-009l-4590101000-9dd75d54ebdad9453641	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9220000000-a43d85cb3e9f582fef66	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 Pubmed: 22753057
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Phosphatidylserine decarboxylase proenzyme

General function:: Involved in phosphatidylserine decarboxylase activity
Specific function:: Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2)
Gene Name:: psd
Uniprot ID:: P0A8K1
Molecular weight:: 35934

Reactions

Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).

Protein Details

2. Bifunctional protein aas

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:: aas
Uniprot ID:: P31119
Molecular weight:: 80699

Reactions

Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].

Protein Details

3. Protein crcA

General function:: Not Available
Specific function:: Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:: crcA
Uniprot ID:: P37001
Molecular weight:: 21770

Protein Details

4. Cardiolipin synthase C

General function:: cardiolipin biosynthetic process
Specific function:: Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:: clsC
Uniprot ID:: P75919
Molecular weight:: 53665

Reactions

Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine

Transporters

Protein Details

1. Probable phospholipid ABC transporter-binding protein mlaB

General function:: Involved in phospholipid transporter activity
Specific function:: Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:: mlaB
Uniprot ID:: P64602
Molecular weight:: 10680

Protein Details

2. Probable phospholipid ABC transporter-binding protein mlaD

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:: mlaD
Uniprot ID:: P64604
Molecular weight:: 19576

Protein Details

3. Probable phospholipid ABC transporter permease protein mlaE

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:: mlaE
Uniprot ID:: P64606
Molecular weight:: 27863

PE(15:0cyclo/14:0(3-OH)) (ECMDB23499) (M2MDB003889)

Structure for #<Compound:0xa4de7cf0>

Enzymes

Reactions

Reactions

Reactions

Transporters