Structure Database (LMSD)

Common Name
Am-LPE(0:0/18:0)
Systematic Name
N-(1-deoxyfructosyl)-2-octadecanoyl-sn-glycero-3-phosphoethanolamine
Synonyms
  • Amadori-LPE 0:0/18:0
LM ID
LMGP21050008
Formula
Exact Mass
Calculate m/z
643.369667
Sum Composition
Abbrev Chains
Am-Hex-LPE 36:0
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)
XBQVYXKSZNUSMM-PMCIJNRMSA-N
InChi (Click to copy)
InChI=1S/C29H58NO12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(33)42-24(20-31)21-41-43(37,38)40-19-18-30-23-29(36)28(35)27(34)25(32)22-39-29/h24-25,27-28,30-32,34-36H,2-23H2,1H3,(H,37,38)/t24-,25-,27-,28+,29-/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(CCCCCCCCCCCCCCCCC)=O)CO

Other Databases

PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 43
Rings 1
Aromatic Rings
Rotatable Bonds 28
Van der Waals Molecular Volume 631.57
Topological Polar Surface Area 206.54
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 13
logP 5.99
Molar Refractivity 165.40

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.