Structure Database (LMSD)

Common Name
Am-PE(18:2/20:4(5Z,8Z,11Z,14Z))
Systematic Name
N-(1-deoxyfructosyl)-1-(9Z,12Z-octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
  • Amadori-PE 18:2/20:4
LM ID
LMGP21010012
Status
Active
Exact Mass
Calculate m/z
925.568032
Formula
Abbrev
Abbrev Chains
Am-Hex-PE 18:2_20:4


Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

String Representations

InChiKey (Click to copy)
WLUAJGBQSBDHGL-KEOVZNOISA-N
InChi (Click to copy)
InChI=1S/C49H84NO13P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(53)63-43(39-59-45(52)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-62-64(57,58)61-38-37-50-42-49(56)48(55)47(54)44(51)41-60-49/h11-14,17-19,21-22,24,28,30,43-44,47-48,50-51,54-56H,3-10,15-16,20,23,25-27,29,31-42H2,1-2H3,(H,57,58)/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t43-,44-,47-,48+,49-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCNC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O)([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Comprehensive Identification of Amadori Compound-Modified Phosphatidylethanolamines in Human Plasma.,
Chem Res Toxicol, 2019
Pubmed ID: 31188577

Calculated Physicochemical Properties

Heavy Atoms 64
Rings 1
Aromatic Rings
Rotatable Bonds 42
Van der Waals Molecular Volume 967.88
Topological Polar Surface Area 212.61
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 14
logP 12.24
Molar Refractivity 257.48

Admin

Created at
11th Aug 2021
Updated at
11th Aug 2021
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.