Structure Database (LMSD)

Common Name
PE-N[FA 20:4(5Z,8Z,11Z,14Z)] P-18:0/22:4(7Z,10Z,13Z,16Z)
Systematic Name
1-(1Z-octadecenyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phospho-N-5Z,8Z,11Z,14Z-eicosatetraenoyl-ethanolamine
Synonyms
  • 1-(1Z-octadecenyl)-2-(adrenoyl)-sn-glycero-3-phospho-N-arachidonoyl-ethanolamine
  • NAPE(P-18:0/22:4(7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))
LM ID
LMGP02030100
Formula
Exact Mass
Calculate m/z
1065.812557
Sum Composition
Status
Active

Classification

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain.,
J Lipid Res, 2008
Pubmed ID: 17957091

String Representations

InChiKey (Click to copy)
LPKZQVPCPFZJGE-IRRBZYEZSA-N
InChi (Click to copy)
InChI=1S/C65H112NO8P/c1-4-7-10-13-16-19-22-25-28-31-32-34-36-39-42-45-48-51-54-57-65(68)74-63(61-71-59-55-52-49-46-43-40-37-30-27-24-21-18-15-12-9-6-3)62-73-75(69,70)72-60-58-66-64(67)56-53-50-47-44-41-38-35-33-29-26-23-20-17-14-11-8-5-2/h16-17,19-20,25-26,28-29,32,34-35,38-39,42,44,47,55,59,63H,4-15,18,21-24,27,30-31,33,36-37,40-41,43,45-46,48-54,56-58,60-62H2,1-3H3,(H,66,67)(H,69,70)/b19-16-,20-17-,28-25-,29-26-,34-32-,38-35-,42-39-,47-44-,59-55-/t63-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCNC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)([H])(OC(CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO/C=C\CCCCCCCCCCCCCCCC

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 75
Rings
Aromatic Rings
Rotatable Bonds 57
Van der Waals Molecular Volume 1205.17
Topological Polar Surface Area 120.39
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 9
logP 21.22
Molar Refractivity 323.02

Admin

Created at
10th Oct 2023
Updated at
10th Oct 2023
LIPID MAPS® abbreviations for glycerophospholipids (GP)

The LIPID MAPS® glycerophospholipid abbreviations (PC, PE, etc.) are used here to refer to species with one or two radyl side-chains where the structures of the side chains are indicated within parentheses in the 'Headgroup(sn1/sn2)' format (e.g. PC(16:0/18:1(9Z)). By default, R stereochemistry at the C-2 carbon of glycerol and attachment of the headgroup at the sn3 position is assumed. Also, acyl chains are assumed by default. The 'O-' prefix is used to indicate the presence of an alkyl ether substituent e.g. PC(O-16:0/18:1(9Z)), whereas the 'P-' prefix is used for the 1Z-alkenyl ether (Plasmalogen) substituent e.g. PC(P-16:0/18:1(9Z)).

For molecules with opposite (S) stereochemistry at C2 of the glycerol group and attachment of the headgroup at the sn1 position, the stereochemistry specification of [S] is appended to the abbreviation. The 'Headgroup(sn3/sn2)' abbreviation format is used.

For molecules with unknown stereochemistry at the C-2 carbon of the glycerol group, the stereochemistry specification of [U] is appended to the abbreviation and the structure is drawn with C-2 stereochemistry unspecified.