Structure Database (LMSD)

Common Name
Am-PE(O-20:0/20:4(5Z,8Z,11Z,14Z))
Systematic Name
N-(1-deoxyfructosyl)-1-eicosanyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
  • Amadori-PE O-20:0/20:4
LM ID
LMGP21020002
Formula
Exact Mass
Calculate m/z
943.651367
Sum Composition
Abbrev Chains
Am-Hex-PE O-20:0/20:4
Status
Active

Classification

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

String Representations

InChiKey (Click to copy)
SJBFZMAGZLCIHG-AFKZUMDCSA-N
InChi (Click to copy)
InChI=1S/C51H94NO12P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-40-60-42-46(43-63-65(58,59)62-41-39-52-45-51(57)50(56)49(55)47(53)44-61-51)64-48(54)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,24,26,30,32,46-47,49-50,52-53,55-57H,3-11,13,15-17,19,21-23,25,27-29,31,33-45H2,1-2H3,(H,58,59)/b14-12-,20-18-,26-24-,32-30-/t46-,47-,49-,50+,51-/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)COCCCCCCCCCCCCCCCCCCCC

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 65
Rings 1
Aromatic Rings
Rotatable Bonds 46
Van der Waals Molecular Volume 1001.61
Topological Polar Surface Area 195.54
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 13
logP 14.22
Molar Refractivity 267.26

Admin

Created at
11th Aug 2021
Updated at
25th Apr 2022
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.