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PG(12:0(3-OH)/18:1(9Z)) (M2MDB004050)

Record Information
Version2.0
Creation Date2012-10-24 09:54:56 -0600
Update Date2015-12-09 12:06:29 -0700
Secondary Accession Numbers
  • ECMDB23660
Identification
Name:PG(12:0(3-OH)/18:1(9Z))
DescriptionPG(12:0(3-OH)/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(12:0(3-OH)/18:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1-3-hydroxydodecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
  • 1-3-hydroxydodecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol
  • 1-3-hydroxydodecanoyl-2-oleoyl-sn-glycero-3-phosphoglycerol
  • GPG(12:0/18:1)
  • GPG(30:1)
  • PG(12:0/18:1)
  • PG(30:1)
  • Phosphatidylglycerol(12:0/18:1)
  • Phosphatidylglycerol(30:1)
Chemical Formula:C36H69O11P
Weight:Average: 708.911
Monoisotopic: 708.45775004
InChI Key:JBYOWJPVFJCYBW-IQAYTRFVSA-N
InChI:InChI=1S/C36H69O11P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-35(40)44-30-34(31-46-48(42,43)45-29-33(39)28-37)47-36(41)27-32(38)25-23-21-19-10-8-6-4-2/h14-15,32-34,37-39H,3-13,16-31H2,1-2H3,(H,42,43)/b15-14-/t32?,33-,34+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:(2S)-2,3-dihydroxypropoxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCC
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Beta-hydroxy acid
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Hydroxy acid
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP6.29ALOGPS
logP8.46ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area169.05 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity188.74 m³·mol⁻¹ChemAxon
Polarizability82.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2 PGP(12:0(3-OH)/18:1(9Z)) + Water >2 PG(12:0(3-OH)/18:1(9Z)) + Phosphate
2 PG(12:0(3-OH)/18:1(9Z)) > Glycerol + CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z))
SMPDB Pathways:
phospholipid biosynthesis (CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z)))PW001924 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-4670639300-623153894b1e8e6de4d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ou-7981547000-fea244ad4702afa1cd99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-9343022000-be30712357f924340cffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06si-0390212200-39e585069d2e652c6211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-5490101000-51e5c8ff059e9175501aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-56d6eb88e9b746b58bd1View in MoNA
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
  • Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16. Pubmed: 4902888
  • 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Lysophospholipase L2
General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
Protein Details
2. Phosphatidylglycerophosphatase B
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
Protein Details
3. Phosphatidylglycerophosphatase A
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:
pgpA
Uniprot ID:
P18200
Molecular weight:
19418
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
Protein Details
4. Lipid A export ATP-binding/permease protein msbA
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460
Protein Details
5. 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
6. 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. Affects resistance to the gyrase inhibitor novobiocin
Gene Name:
cls
Uniprot ID:
P0A6H8
Molecular weight:
54822
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
Protein Details
7. Putative cardiolipin synthase ybhO
General function:
Involved in catalytic activity
Specific function:
Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
Gene Name:
ybhO
Uniprot ID:
P0AA84
Molecular weight:
47633
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

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. Lipid A export ATP-binding/permease protein msbA
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460
Protein Details
3. 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
4. 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