PG(16:0/16:1(11Z)) (YMDB14942)

Identification

YMDB ID

YMDB14942

Name

PG(16:0/16:1(11Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PG(16:0/16:1(11Z)) 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(16:0/16:1(11Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 11Z-hexadecenoyl 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

Not Available

CAS number

Not Available

Weight

Average: 720.966
Monoisotopic: 720.494135549

InChI Key

DJFPNCZPVOWEMA-PTINEBJGSA-N

InChI

InChI=1S/C38H73O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h10,12,35-36,39-40H,3-9,11,13-34H2,1-2H3,(H,43,44)/b12-10-/t35-,36+/m0/s1

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-(hexadecanoyloxy)propoxy]phosphinic acid

Traditional IUPAC Name

(2S)-2,3-dihydroxypropoxy((2R)-2-[(11Z)-hexadec-11-enoyloxy]-3-(hexadecanoyloxy)propoxy)phosphinic acid

Chemical Formula

C₃₈H₇₃O₁₀P

SMILES

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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	0.00014 g/L	ALOGPS
logP	7.73	ALOGPS
logP	10.58	ChemAxon
logS	-6.7	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	39	ChemAxon
Refractivity	196.43 m³·mol⁻¹	ChemAxon
Polarizability	86.12 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

Mitochondrion membrane

Organoleptic Properties

Not Available

SMPDB Pathways

Cardiolipin Biosynthesis CL(16:0/16:1(11Z)/16:0/16:1(11Z))	PW012460
Cardiolipin Biosynthesis CL(16:0/16:1(11Z)/16:0/16:1(9Z))	PW012461
Cardiolipin Biosynthesis CL(16:0/16:1(11Z)/16:1(11Z)/16:1(11Z))	PW012462
Cardiolipin Biosynthesis CL(16:0/16:1(11Z)/16:1(11Z)/16:1(9Z))	PW012463
Cardiolipin Biosynthesis CL(16:0/16:1(11Z)/16:1(11Z)/18:0)	PW012464

KEGG Pathways

Not Available

SMPDB Reactions

PGP(16:0/16:1(11Z)) + water → phosphate + PG(16:0/16:1(11Z))

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

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

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

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

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
13000 ± 1025 umol/L	SD media with 2% raffinose	24 oC	BY4741	PMID: 19174513
7000 ± 9975 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_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-14i0-0091300000-c814d4c5b8813d16934f	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:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

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
FOODB ID	Not Available
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:0xa733ec38>

Enzymes

Reactions

Reactions