ECMDB: PG(18:1(9Z)/18:1(9Z)) (ECMDB24136) (M2MDB006253)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (5)

Record Information

Version

2.0

Creation Date

2015-09-08 17:49:36 -0600

Update Date

2015-12-09 17:02:33 -0700

Secondary Accession Numbers

ECMDB24136

Identification

Name:

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

Description

PG(18:1(9Z)/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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl chains at positions C-1 and C-2. 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

Chemical Formula:

C₄₂H₇₉O₁₀P

Weight:

Average: 775.058
Monoisotopic: 774.541085742

InChI Key:

DSNRWDQKZIEDDB-VGHPCWFHSA-N

InChI:

InChI=1S/C42H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48)/b19-17-,20-18-/t39-,40-/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

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

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

Not Available

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	8.4e-05 g/L	ALOGPS
logP	8.47	ALOGPS
logP	11.99	ChemAxon
logS	-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	42	ChemAxon
Refractivity	215.95 m³·mol⁻¹	ChemAxon
Polarizability	93.09 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:

More...

SMPDB Pathways:

phospholipid biosynthesis (CL(17:0cycw7c/12:0(3-OH)/17:0cycw7c/12:0(3-OH)))	PW001970
phospholipid biosynthesis (CL(17:0cycw7c/18:1(9Z)/14:0/18:1(9Z)))	PW001712
phospholipid biosynthesis (CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/18:1(9Z)))	PW001466
phospholipid biosynthesis (CL(17:0cycw7c/18:1(9Z)/18:1(9Z)/14:0))	PW001473
phospholipid biosynthesis (CL(18:1(9Z)/14:0/14:0/18:1(9Z)))	PW001494
phospholipid biosynthesis (CL(18:1(9Z)/14:0/18:1(9Z)/14:0))	PW001500
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo))	PW001531
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/16:0))	PW001532
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/16:1(9Z)))	PW001533
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/18:1(9Z)))	PW001540
phospholipid biosynthesis (CL(18:1(9Z)/16:0/17:0cycw7c/18:1(9Z)))	PW001586
phospholipid biosynthesis (CL(18:1(9Z)/16:0/18:1(9Z)/17:0cycw7c))	PW001595
phospholipid biosynthesis (CL(18:1(9Z)/16:0/18:1(9Z)/19:0cycv8c))	PW001597
phospholipid biosynthesis (CL(18:1(9Z)/16:0/19:0cycv8c/18:1(9Z)))	PW001599
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/17:0cycw7c/18:1(9Z)))	PW001619
phospholipid biosynthesis (CL(18:1(9Z)/17:0cycw7c/14:0/18:1(9Z)))	PW001635
phospholipid biosynthesis (CL(18:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z)))	PW001644
phospholipid biosynthesis (CL(18:1(9Z)/17:0cycw7c/18:1(9Z)/14:0))	PW001646
phospholipid biosynthesis (CL(18:1(9Z)/17:0cycw7c/18:1(9Z)/17:0cycw7c))	PW001647
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/14:0))	PW001649
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/15:0cyclo))	PW001664
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/16:0))	PW001665
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/16:1(9Z)))	PW001666
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/17:0cycw7c))	PW001667
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/18:1(9Z)))	PW001668
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/14:0/19:0cycv8c))	PW001669
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/14:0))	PW001670
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/15:0cyclo))	PW001671
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/16:0))	PW001672
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/16:1(9Z)))	PW001673
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/18:1(9Z)))	PW001680
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/19:0cycv8c))	PW001685
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/14:0))	PW001686
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/17:0cycw7c))	PW001687
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c))	PW001026
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c)) 1440195714	PW001034
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c)) 2	PW001186
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/14:0))	PW001688
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/15:0cyclo))	PW001185
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/16:0))	PW001194
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/16:0)) 1442332377	PW001956
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/16:1(9Z))	PW001212
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/19:0cycv8c/17:0cycw7c))	PW001210
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/17:0cycw7c/18:1(9Z)))	PW001241
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/18:1(9Z)/17:0cycw7c))	PW001248
phospholipid biosynthesis (CL(18:1/18:1/18:1/18:1))	PW001027
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z)))	PW001415
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/17:0cycw7c/18:1(9Z)))	PW001423
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/18:1(9Z)/14:0))	PW001424
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/18:1(9Z)/17:0cycw7c))	PW001426
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/18:1(9Z))	PW001085
phospholipid biosynthesis CL(15:0cyclo/16:0/18:1(9Z)/18:1(9Z))	PW001113
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/18:1(9Z))	PW001138
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/18:1(9Z)/18:1(9Z))	PW001157
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/14:0/18:1(9Z))	PW001160
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/15:0cyclo/18:1(9Z))	PW001163
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/16:0/18:1(9Z))	PW001166
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/16:1(9Z)/18:1(9Z))	PW001168
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/17:0cycw7c/18:1(9Z))	PW001171
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/14:0)	PW001172
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/15:0cyclo)	PW001173
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/16:0)	PW001174
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/16:1(9Z))	PW001175
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/17:0cycw7c)	PW001176
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/18:1(9Z))	PW001177
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/19:0cycv8c)	PW001178
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/19:0cycv8c/18:1(9Z))	PW001180
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/18:1(9Z)/18:1(9Z))	PW001196
phospholipid biosynthesis CL(16:0/14:0/18:1(9Z)/18:1(9Z))	PW001217
phospholipid biosynthesis CL(16:0/15:0cyclo/18:1(9Z)/18:1(9Z))	PW001243
phospholipid biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))	PW001330
phospholipid biosynthesis CL(16:0/17:0cycw7c/18:1(9Z)/18:1(9Z))	PW001352
phospholipid biosynthesis CL(16:0/18:1(9Z)/14:0/18:1(9Z))	PW001357
phospholipid biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))	PW001363
phospholipid biosynthesis CL(16:0/18:1(9Z)/17:0cycw7c/18:1(9Z))	PW001366
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/14:0)	PW001367
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/17:0cycw7c)	PW001370
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))	PW001371
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/19:0cycv8c)	PW001378
phospholipid biosynthesis CL(16:0/18:1(9Z)/19:0cycv8c/18:1(9Z))	PW001380
phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/18:1(9Z))	PW001402
phospholipid biosynthesis CL(16:1(9Z)/14:0/18:1(9Z)/18:1(9Z))	PW001427
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/18:1(9Z))	PW001462
phospholipid biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))	PW001504
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/18:1(9Z)/18:1(9Z))	PW001568
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/18:1(9Z))	PW001573
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/17:0cycw7c/18:1(9Z))	PW001592
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/14:0)	PW001593
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/17:0cycw7c)	PW001603
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))	PW001604
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c)	PW001605
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/18:1(9Z))	PW001611
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/18:1(9Z)/18:1(9Z))	PW001636

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

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	splash10-056u-5161813900-bd1dc51abd2d8e880c90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0axu-9284805300-b825e480cfd129d8714c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ay0-9056424100-68d324ee98fbcce7dd03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01x0-1190211400-1a2e657158602c30b617	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-5290201000-6ad13dad9756ffd272d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9010100000-21182955d9fc9d49a7a1	View 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
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	76956060
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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

2. 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

3. 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

4. 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.

Protein Details

5. Cardiolipin synthase C

General function:: cardiolipin biosynthetic process
Specific function:: Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:: clsC
Uniprot ID:: P75919
Molecular weight:: 53665

Reactions

Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine

PG(18:1(9Z)/18:1(9Z)) (ECMDB24136) (M2MDB006253)

Structure for #<Compound:0x9c153b04>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions