ECMDB: PS(17:0/17:0) (ECMDB21056) (M2MDB001472)

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

Proteins (6)

Record Information

Version

2.0

Creation Date

2012-05-31 14:56:35 -0600

Update Date

2015-12-09 12:10:47 -0700

Secondary Accession Numbers

ECMDB21056

Identification

Name:

PS(17:0/17:0)

Description

PS(17:0/17:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(17:0/17:0), in particular, consists of two heptadecanoyl chains at positions C-1 and C-2. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. 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. Phosphatidylserines typically carry a net charge of -1 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. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1,2-diheptadecanoyl-rac-glycero-3-phosphoserine
1,2-diheptadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)
1,2-dimargaroyl-rac-glycero-3-phosphoserine
Phosphatidylserine(17:0/17:0)
Phosphatidylserine(34:0)
PS(34:0)
PSer(17:0/17:0)
PSer(34:0)

Chemical Formula:

C₄₀H₇₈NO₁₀P

Weight:

Average: 764.035
Monoisotopic: 763.536334714

InChI Key:

SCWVNRVOGVIXNF-AARKOHAPSA-N

InChI:

InChI=1S/C40H78NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-38(42)48-33-36(34-49-52(46,47)50-35-37(41)40(44)45)51-39(43)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h36-37H,3-35,41H2,1-2H3,(H,44,45)(H,46,47)/t36-,37+/m1/s1

CAS number:

Not Available

IUPAC Name:

(2S)-2-amino-3-({[(2R)-2,3-bis(heptadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional IUPAC Name:

(2S)-2-amino-3-{[(2R)-2,3-bis(heptadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

SMILES:

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines 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

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Amino acid
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Carbonyl group
Hydrocarbon derivative
Primary amine
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010895 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.3e-05 g/L	ALOGPS
logP	4.66	ALOGPS
logP	10.38	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	206.04 m³·mol⁻¹	ChemAxon
Polarizability	92.23 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

Biological Properties

Cellular Locations:

Membrane

Reactions:

PS(17:0/17:0) + Hydrogen ion > Carbon dioxide + PE(17:0/17:0)
PS(17:0/17:0) + Hydrogen ion > PE(17:0cycw7c/17:0cycw7c) + Carbon dioxide

SMPDB Pathways:

phospholipid biosynthesis (CL(17:0cycw7c/17:0cycw7c/17:0cycw7c/14:0))	PW001708
phospholipid biosynthesis (CL(17:0cycw7c/17:0cycw7c/17:0cycw7c/17:0cycw7c))	PW001709
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/14:0/17:0cycw7c))	PW001476
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/17:0cycw7c/14:0))	PW001483
phospholipid biosynthesis (CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c))	PW001499
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/17:0cycw7c/17:0cycw7c))	PW001302
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/17:0cycw7c/17:0cycw7c))	PW001447
phospholipid biosynthesis CL(15:0cyclo/14:0/17:0cycw7c/17:0cycw7c)	PW001056
phospholipid biosynthesis CL(15:0cyclo/16:0/17:0cycw7c/17:0cycw7c)	PW001110
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001135
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/14:0/17:0cycw7c)	PW001143
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/16:0/17:0cycw7c)	PW001146
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/16:1(9Z)/17:0cycw7c)	PW001148
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c)/16:0)	PW001151
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c/16:1(9Z))	PW001152
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c/17:0cycw7c)	PW001153
phospholipid biosynthesis CL(16:0/14:0/17:0cycw7c/17:0cycw7c)	PW001215
phospholipid biosynthesis CL(16:0/15:0cyclo/17:0cycw7c/17:0cycw7c)	PW001238
phospholipid biosynthesis CL(16:0/16:0/17:0cycw7c/17:0cycw7c)	PW001274
phospholipid biosynthesis CL(16:0/16:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001327
phospholipid biosynthesis CL(16:0/17:0cycw7c/14:0/17:0cycw7c)	PW001339
phospholipid biosynthesis CL(16:0/17:0cycw7c/16:0/17:0cycw7c)	PW001343
phospholipid biosynthesis CL(16:0/17:0cycw7c/16:1(9Z)/17:0cycw7c)	PW001345
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/14:0)	PW001346
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/16:1(9Z))	PW001347
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/17:0cycw7c)	PW001351
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/18:1(9Z))	PW001348
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/19:0cycv8c)	PW001349
phospholipid biosynthesis CL(16:0/17:0cycw7c/18:1(9Z)/17:0cycw7c)	PW001350
phospholipid biosynthesis CL(16:0/17:0cycw7c/19:0cycv8c/17:0cycw7c)	PW001353
phospholipid biosynthesis CL(16:0/18:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001365
phospholipid biosynthesis CL(16:0/19:0cycv8c/17:0cycw7c/17:0cycw7c)	PW001400
phospholipid biosynthesis CL(16:1(9Z)/14:0/17:0cycw7c/17:0cycw7c)	PW001421
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/17:0cycw7c/17:0cycw7c)	PW001459
phospholipid biosynthesis CL(16:1(9Z)/16:0/17:0cycw7c/17:0cycw7c)	PW001497
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001539
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/14:0/17:0cycw7c)	PW001559
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/16:1(9Z)/17:0cycw7c)	PW001561
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/14:0)	PW001562
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/16:1(9Z))	PW001563
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/17:0cycw7c)	PW001564
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z))	PW001565
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/19:0cycv8c)	PW001566
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/17:0cycw7c)	PW001567
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/19:0cycv8c/17:0cycw7c)	PW001569
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001591
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/17:0cycw7c/17:0cycw7c)	PW001628
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/14:0/17:0cycw7c)	PW001651
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/16:0/17:0cycw7c)	PW001652
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/16:1(9Z)/17:0cycw7c)	PW001653
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/14:0)	PW001654
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/16:0)	PW001656
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/16:1(9Z))	PW001657
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/17:0cycw7c)	PW001658
phospholipid biosynthesis CL(17:0cycw7c/16:0/14:0/17:0cycw7c)	PW001674
phospholipid biosynthesis CL(17:0cycw7c/16:0/16:0/17:0cycw7c)	PW001676
phospholipid biosynthesis CL(17:0cycw7c/16:0/16:1(9Z)/17:0cycw7c)	PW001677
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/14:0)	PW001678
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/16:0)	PW001681
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/16:1(9Z))	PW001682
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/17:0cycw7c)	PW001683
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z))	PW001684
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/19:0cycv8c)	PW001689
phospholipid biosynthesis CL(17:0cycw7c/16:0/18:1(9Z)/17:0cycw7c)	PW001690
phospholipid biosynthesis CL(17:0cycw7c/16:0/19:0cycv8c/17:0cycw7c)	PW001691

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

phospholipid biosynthesis I PHOSLIPSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	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
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
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	46891783
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. 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

3. CDP-diacylglycerol--serine O-phosphatidyltransferase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
Gene Name:: pssA
Uniprot ID:: P23830
Molecular weight:: 52801

Reactions

CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine.

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

PS(17:0/17:0) (ECMDB21056) (M2MDB001472)

Structure for #<Compound:0xb24ae338>

Enzymes

Reactions

Reactions

Transporters