Structure Database (LMSD)

Common Name
PHOHA-PE
Systematic Name
1-hexadecanoyl-2-(4-hydroxy-7-oxo-5E-heptenoyl)-sn-glycero-3-phosphoethanolamine
Synonyms
  • 1-palmitoyl-2-(4-hydroxy-7-oxo-5E-heptenoyl)-sn-glycero-3-phosphoethanolamine
LM ID
LMGP20020019
Formula
Exact Mass
Calculate m/z
593.332887
Sum Composition
Status
Active

Classification

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Oxidized phospholipids as endogenous pattern recognition ligands in innate immunity.,
J Biol Chem, 2008
Pubmed ID: 18285328

String Representations

InChiKey (Click to copy)
UYWHOTHDXIKERB-ZTUGMGODSA-N
InChi (Click to copy)
InChI=1S/C28H52NO10P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-27(32)36-23-26(24-38-40(34,35)37-22-20-29)39-28(33)19-18-25(31)16-15-21-30/h15-16,21,25-26,31H,2-14,17-20,22-24,29H2,1H3,(H,34,35)/b16-15+/t25?,26-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCCN)([H])(OC(CCC(O)/C=C/C(=O)[H])=O)COC(CCCCCCCCCCCCCCC)=O

Other Databases

CHEBI ID
PubChem CID

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 0
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 601.13
Topological Polar Surface Area 171.68
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 11
logP 6.79
Molar Refractivity 155.23

Admin

Created at
-
Updated at
8th Nov 2024
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.