Shorthand notation for Glycerophospholipids (GP)

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**'''P = proven O-alk-1-enyl-bond''' (acid-sensitive ether bond in “plasmalogens”).  
**'''P = proven O-alk-1-enyl-bond''' (acid-sensitive ether bond in “plasmalogens”).  
*More than one "non"-ester bond is indicated in front of the bond type as d for di, t for tri.  
*More than one "non"-ester bond is indicated in front of the bond type as d for di, t for tri.  
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*Lysophospholipid classes are abbreviated as stated in the LIPID MAPS nomenclature (Table 1). Where applicable they can be presented formally by their respective phospholipid class indicating the empty sn-position by 0:0.  
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*Lysophospholipid classes are abbreviated as stated in the [http://www.lipidmaps.org/data/classification/LM_classification_exp.php LIPID MAPS nomenclature]. Where applicable they can be presented formally by their respective phospholipid class indicating the empty sn-position by 0:0.  
*Four ether bonds are indicated in front of the bond type as tetra, abbreviated e.  
*Four ether bonds are indicated in front of the bond type as tetra, abbreviated e.  
*For BMP and CL classes the sn-position order will be sn-2/sn-3/sn-2'/sn-3' and sn-1/sn-2/sn-1'/sn-2', respectively.  
*For BMP and CL classes the sn-position order will be sn-2/sn-3/sn-2'/sn-3' and sn-1/sn-2/sn-1'/sn-2', respectively.  
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*Rules for phosphoinositides require additional information if the position of phosphates on the inositol ring are known (see Table 4B). The exception is PI3,4,5P3 since the only known tris isomer is 3,4,5. Whilst phosphoinositides are generally presented as PIP2 and PIP3 in Tables 1 and 4 we have adopted the annotation PIP2 and PIP3 for ease of handling by databases. Should additional species be identified this will require further clarification.
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*Rules for phosphoinositides require additional information if the position of phosphates on the inositol ring are known. The exception is PI3,4,5P3 since the only known tris isomer is 3,4,5. Whilst phosphoinositides are generally presented as PIP2 and PIP3 we have adopted the annotation PIP2 and PIP3 for ease of handling by databases. Should additional species be identified this will require further clarification.
= Lipid class abbreviations  =
= Lipid class abbreviations  =

Revision as of 15:44, 28 October 2015

Rules for the annotation

  • Shorthand notation: Lipid class abbreviation followed by number of C-atoms:number of double bonds.
  • Fatty acids linked to the glycerol are known:
    • separator _: sn-position of the fatty acids is not known
    • separator /: sn-position of fatty acids is proven (order sn-1/sn-2/sn-3 for GL; sn-1/sn-2 or sn-2/sn-3 for GP); no FA linked 0:0
  • Other bond types than ester bonds are indicated as follows in front of the sum of C-atoms or fatty acid:
    • O = proven O-alkyl-bond (it is important to note that “O” after the number of carbons designates a keto bond)
    • P = proven O-alk-1-enyl-bond (acid-sensitive ether bond in “plasmalogens”).
  • More than one "non"-ester bond is indicated in front of the bond type as d for di, t for tri.
  • Lysophospholipid classes are abbreviated as stated in the LIPID MAPS nomenclature. Where applicable they can be presented formally by their respective phospholipid class indicating the empty sn-position by 0:0.
  • Four ether bonds are indicated in front of the bond type as tetra, abbreviated e.
  • For BMP and CL classes the sn-position order will be sn-2/sn-3/sn-2'/sn-3' and sn-1/sn-2/sn-1'/sn-2', respectively.
  • Rules for phosphoinositides require additional information if the position of phosphates on the inositol ring are known. The exception is PI3,4,5P3 since the only known tris isomer is 3,4,5. Whilst phosphoinositides are generally presented as PIP2 and PIP3 we have adopted the annotation PIP2 and PIP3 for ease of handling by databases. Should additional species be identified this will require further clarification.

Lipid class abbreviations

  • Bismonoacylglycerolphosphate - BMP
  • Cardiolipin - CL
  • Phosphatidic acid - PA
  • Phosphatidylcholine - PC
  • Phosphatidylethanolamine - PE
  • Phosphatidylgylcerol - PG
  • Phosphatidylgylcerolphosphate - PGP
  • Phosphatidylinositol - PI
  • Phosphatidylinositol-monophosphate - PIP
  • Phosphatidylinositol-3-phosphate - PIP[3’]
  • Phosphatidylinositol-4-phosphate - PIP[4’]
  • Phosphatidylinositol-5-phosphate - PIP[5’]
  • Phosphatidylinositol-bisphosphate - PIP2
  • Phosphatidylinositol-3,4-bisphosphate - PIP2[3’,4’]
  • Phosphatidylinositol-3,5-bisphosphate - PIP2[3’,5’]
  • Phosphatidylinositol-4,5-bisphosphate - PIP2[4’,5’]
  • Phosphatidylinositol-trisphosphate – PIP3
  • Phosphatidylserine – PS
  • Lysophospholipids - Prefix L


Examples

Bond type
Lipid class level mass$
Lipid species level§
Bond type level
Fatty acyl/alkyl level
Fatty acyl/alkyl position level
LIPID MAPS Fatty acyl/alkyl structure level
Diacyl
BMP (690)
BMP 34:2
BMP 34:2
BMP 16:0_18:2
BMP 16:0/0:0/18:2/0:0
BMP 16:0/0:0/18:2(9Z,12Z)/0:0





sn-2/sn-3/sn-2'/sn-3'
sn-2/sn-3/sn-2'/sn-3'
Tetraacyl
CL (1450)
CL 72:7
CL 72:7
CL 18:1_18:2_18:2_18:2
CL 18:1/18:2/18:2/18:2
CL 18:1(9Z)/18:2(9Z,12Z)/ 18:2(9Z,12Z)/18:2(9Z,12Z)




CL 36:3_36:4 (known DG fragments)
sn-1/sn-2/sn-1'/sn-2'
sn-1/sn-2/sn-1'/sn-2'
Tetraalkyl
CL (1521)
CL 76:0
CL eO-80:0
CL O-20:0/O-20:0/O‑20:0 /O-20:0
CL O-20:0/O-20:0/O-20:0/ O‑20:0
CL O‑16:0(3Me,7Me,11Me,15Me)/ O‑16:0(3Me,7Me,11Me,15Me)/ O‑16:0(3Me,7Me,11Me,15Me)/ O‑16:0(3Me,7Me,11Me,15Me)
Diacyl
PC (759)
PC 34:1
PC 34:1
PC 16:0_18:1
PC 16:0/18:1
PC 16:0/18:1(9Z)
Alkyl-acyl
PC (745)
PC O-34:1
PC O-34:1
PC O-16:0_18:1
PC O-16:0/18:1
PC O-16:0/18:1(9Z)
Dialkyl
PC (731)
PC 32:1
PC dO-34:1
PC O-16:0_O-18:1
PC O-16:0/O-18:1
PC O-16:0/O-18:1
Diacyl
PE (717)
PE 34:1
PE 34:1
PE 16:0_18:1
PE 16:0/18:1
PE 16:0/18:1(9Z)
Plasmalogen
PE (701)
PE O-34:2
PE O-34:2
PE P-16:0_18:1 %
PE P-16:0/18:1 %
PE P-16:0/18:1(9Z)
Triacyl
LCL (1188)
LCL 54:5
LCL 54:5
LCL 18:1_18:2_18:2
LCL 18:1/18:2/18:2/0:0
LCL 18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/0:0
Acyl
LPC (495)
LPC 16:0
LPC 16:0
LPC 16:0 or PC 16:0_0:0
LPC 16:0/0:0 or PC 16:0/0:0
LPC 16:0/0:0 or PC 16:0/0:0
Alkyl
LPC (481)
LPC O-16:0
LPC O-16:0
LPC O-16:0
LPC O-16:0/0:0
LPC O-16:0/0:0
Alkyl/Alk-1-enyl
LPC (479)
LPC O-16:1
LPC O-16:1
LPC O-16:1
LPC O-16:1/0:0
LPC O-16:1(9Z)/0:0

$ m is the uncharged molecular mass
§ Annotation based on assumption of even numbered carbon chains only
 % Identification of plasmalogens (alk-1-enyl bond) require specific MS analysis

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