PG(16:0/18:1(9Z)) (YMDB01210)

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Identification

YMDB ID

YMDB01210

Name

PG(16:0/18:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PG(16:0/18:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoglycerol
GPG(16:0/18:1)
GPG(16:0/18:1n9)
GPG(16:0/18:1w9)
GPG(34:1)
PG(16:0/18:1)
PG(16:0/18:1n9)
PG(16:0/18:1w9)
PG(34:1)
Phosphatidylglycerol(16:0/18:1)
Phosphatidylglycerol(16:0/18:1n9)
Phosphatidylglycerol(16:0/18:1w9)
Phosphatidylglycerol(34:1)
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-sn-glycerol
1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol)
16:0/18:1 PG
C16:0/18:1 PG
GPG(16:0/18:1OMEGA9)
PG(16:0/18:1OMEGA9)
Phosphatidylglycerol(16:0/18:1omega9)
PG(16:0/18:1(9Z))
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol
1-Palmitoyl-2-oleoyl-GPG
1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-glycerol)
1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1’-glycerol)
Phosphatidylglycerol(16:0/18:1(9Z))
GPG(16:0/18:1(9Z))

CAS number

66322-31-4

Weight

Average: 749.0071
Monoisotopic: 748.525435196

InChI Key

PAZGBAOHGQRCBP-HGWHEPCSSA-N

InChI

InChI=1S/C40H77O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46)/b18-17-/t37-,38+/m0/s1

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid

Traditional IUPAC Name

(2S)-2,3-dihydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid

Chemical Formula

C₄₀H₇₇O₁₀P

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols 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

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:73234 )
Diacylglycerophosphoglycerols (LMGP04010987 )

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	8.16	ALOGPS
logP	11.46	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	205.63 m³·mol⁻¹	ChemAxon
Polarizability	90.76 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

Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(11Z))	PW012613
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))	PW012614
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))	PW012615
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))	PW012616
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:0)	PW012617

KEGG Pathways

Not Available

SMPDB Reactions

PGP(16:0/18:1(9Z)) + water → phosphate + PG(16:0/18:1(9Z))

PG(16:0/18:1(9Z)) + CDP-DG(16:0/18:1(11Z)) → Cytidine monophosphate + hydron + CL(16:0/18:1(9Z)/16:0/18:1(11Z))

PG(16:0/18:1(9Z)) + CDP-DG(16:0/18:1(9Z)) → Cytidine monophosphate + hydron + CL(16:0/18:1(9Z)/16:0/18:1(9Z))

PG(16:0/18:1(9Z)) + CDP-DG(18:1(11Z)/18:1(11Z)) → Cytidine monophosphate + hydron + CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))

PG(16:0/18:1(9Z)) + CDP-DG(18:1(11Z)/18:1(9Z)) → Cytidine monophosphate + hydron + CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
5750 ± 8125 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 (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_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	splash10-017s-3190510500-a232a0e6b31e206456a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p0-3291211100-ce1f407ae16906efc250	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-8193121000-0af2bf193e46a0bed9cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a5j-0190200200-a2eadc8237be8cb5a4e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adr-4290100000-2968fa6dd408cb021628	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9030100000-e323076807b814672f5e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000900-2b6e33dc3e3568f4d2fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a61-0090300400-f3f2ad392aa2f94f83cd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053s-0190300400-41a2c1de2632833af2ef	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:

Not Available

External Links:

Resource	Link
CHEBI ID	73234
HMDB ID	HMDB10574
Pubchem Compound ID	119120
Kegg ID	Not Available
ChemSpider ID	25057750
FOODB ID	FDB027724
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Cardiolipin synthase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol
Gene Name:: CRD1
Uniprot ID:: Q07560
Molecular weight:: 32019.30078

Reactions

2 Phosphatidylglycerol → diphosphatidylglycerol + glycerol.

Protein Details

2. Phosphatidylglycerophosphatase GEP4, mitochondrial

General function:: Involved in phosphatidylglycerophosphatase activity
Specific function:: Phosphatidylglycerophosphatase involved in the biosynthesis of cardiolipin (CL), a unique dimeric phosphoglycerolipid predominantly present in mitochondrial membranes and which has important functions for cellular energy metabolism, mitochondrial dynamics and the initiation of apoptotic pathways. Required for the stability of respiratory chain supercomplexes and for growth at elevated temperature, in presence of ethidium bromide or in absence of prohibitins
Gene Name:: GEP4
Uniprot ID:: P38812
Molecular weight:: 20944.90039

Reactions

Phosphatidylglycerophosphate + H(2)O → phosphatidylglycerol + phosphate.

Structure for #<Compound:0xb0ccb9b4>

Enzymes

Reactions

Reactions