PS(16:0/16:0) (YMDB01251)

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Identification

YMDB ID

YMDB01251

Name

PS(16:0/16:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PS(16:0/16:0) 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(16:0/16:0), in particular, consists of two hexadecanoyl 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-D-phosphatidyl-L-serine
1,2-Diacyl-sn-glycerol 3-phospho-L-serine
1,2-dipalmitoyl-rac-glycero-3-phosphoserine
1,2-Dipalmitoylglycerophosphorylserine
1,2-Dipalmitoylphosphatidylserine
3-L-phosphatidyl-L-serine
3-O-sn-Phosphatidyl-L-serine
3-sn-phosphatidyl-L-serines
Dipalmitoyl-DL-a-phosphatidyl-L-serine
Dipalmitoyl-DL-alpha-phosphatidyl-L-serine
Dipalmitoylglycerophosphoserine
Dipalmitoylphosphatidylserine
DL-a-Dipalmitoyl phosphatidyl-L-serine
DL-alpha-Dipalmitoyl phosphatidyl-L-serine
DPPS
L-alpha-phosphatidylserine
O3-Phosphatidyl-L-serine
Phosphatidyl-L-serine
Phosphatidylserine
Phosphatidylserine (16:0/16:0)
Phosphatidylserine (32:0)
Phosphatidylserine(16:0/16:0)
Phosphatidylserine(32:0)
PS(16:0/16:0)
PS(32:0)
PSer(16:0/16:0)
PSer(32:0)
1,2-Dipalmitoyl-sn-glycero-3-phosphoserine
1,2-Dihexadecanoyl-rac-glycero-3-phosphoserine
1,2-Dipalmitoyl-GPS
1,2-Dipalmitoyl-sn-3-glycerophosphoserine
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylserine
1,2-Dipalmitoyl-sn-glycero-3-phospho-L-serine
Dipalmitoyl-sn-glycerol-3-phosphorylserine
L-alpha-Dipalmitoylphosphatidylserine
L-Α-dipalmitoylphosphatidylserine

CAS number

3036-82-6

Weight

Average: 735.981
Monoisotopic: 735.505034585

InChI Key

KLFKZIQAIPDJCW-GPOMZPHUSA-N

InChI

InChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1

IUPAC Name

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

Traditional IUPAC Name

dipalmitoyl phosphatidylserine

Chemical Formula

C₃₈H₇₄NO₁₀P

SMILES

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

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
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-sn-phosphatidyl-L-serine (CHEBI:84523 )
Diacylglycerophosphoserines (LMGP03010029 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0001 g/L	ALOGPS
logP	4.32	ALOGPS
logP	9.49	ChemAxon
logS	-6.8	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	40	ChemAxon
Refractivity	196.83 m³·mol⁻¹	ChemAxon
Polarizability	88.45 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

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Glycerophospholipid metabolism	PW002493
Lysolipid incorporation into ER PC(16:0/16:0)	PW002784
Lysolipid incorporation into Mitochondria PC(16:0/16:0)	PW002753

KEGG Pathways

Glycerophospholipid metabolism	ec00564
Glycine, serine and threonine metabolism	ec00260

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
3000 ± 700 umol/L	SD media with 2% raffinose	24 oC	BY4741	PMID: 19174513
13750 ± 1675 umol/L	SD media with 2% raffinose	37 oC	BY4741	PMID: 19174513
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0000393000-5d82d8d3c3cc3a8e1ef7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0000016900-6bb9b6bacde6d8b4611b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000002900-eaf2a2217a8f79f1c16c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090033100-708416ca737a3b1fee06	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000010900-db7bc8c2e3b9dad9960c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0001391600-51c373de4449f596bd5c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0001391100-9a4a9ad709f158064e08	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-14i6-0000099900-38c346454df0c2d55b3a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k96-0900099900-cf1ed9c46228bdf4f23f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-0900099900-cf1ed9c46228bdf4f23f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-402c44be8653ebc0c284	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000001900-2b5ae18fbcabd46b8f69	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-0166109600-e8d10538897e7b62801e	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513

Synthesis Reference:

Hermetter, A.; Paltauf, F.; Hauser, H. Synthesis of diacyl and alkylacyl glycerophosphoserines. Chemistry and Physics of Lipids (1982), 30(1), 35-45.

External Links:

Resource	Link
CHEBI ID	11750
HMDB ID	HMDB00614
Pubchem Compound ID	3081382
Kegg ID	C02737
ChemSpider ID	7826040
FOODB ID	FDB022144
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xb1210c94>