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Lysophosphatidylethanolamine

Athanor · official

C21H44NO7P · 453.5 g/mol

IUPAC name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] hexadecanoate

Also called LPE, monoacyl phosphatidylethanolamine

Lipids
Open in Athanor
The structure of Lysophosphatidylethanolamine
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
[(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] hexadecanoate
Synonyms
LPE, monoacyl phosphatidylethanolamine, 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine
+ 38 more

1-palmitoyl-sn-glycero-3-phosphoethanolamine, LPE(16:0/0:0), 16:0 LYSO-PE, PE(16:0/0:0), 1-16:0-lysoPE, CHEBI:73134, 1-Palmitoyl-sn-glycerol-3-L-alpha-phosphorylethanolamine, [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] hexadecanoate, ((2R)-3-(2-aminoethoxy(hydroxy)phosphoryl)oxy-2-hydroxypropyl) hexadecanoate, RefChem:935093, 2-azaniumylethyl ((2R)-3-hexadecanoyloxy-2-hydroxypropyl) phosphate, LPE(16:0), 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine, 1-Palmitoyl-2-hydroxy-sn-glycero-3-PE, Lyso-PE(16:0), Lyso-PE(16:0/0:0), Lysophosphatidylethanolamine(16:0), Lysophosphatidylethanolamine(16:0/0:0), 1-Palmitoyl-sn-glycerophosphatidylethanolamine, C21H44NO7P, (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl palmitate, (2R)-3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-hydroxypropyl hexadecanoate, 1-Palmitoyl-2-Hydroxy-sn-Glycero-3-Phosphatidylethanolamine, (2R)-3-[(2-azaniumylethyl phosphonato)oxy]-2-hydroxypropyl hexadecanoate, SCHEMBL274798, orb1985153, 1-palmitoyl-phosphatidylethanolamine, 1-palmitoyl-phosphatidylethenolamine, DCA86235, 1-16:0-lysophosphatidylethanolamine, LMGP02050002, MFCD00133429, AKOS027379128, AS-66193, DA-49193, HY-141617, CS-0182607, PE 16:0/0:0

Molecular formula
C21H44NO7P
Empirical formula
C21H44NO7P
Molecular weight
453.5 g/mol
Exact mass
453.28554
CAS number
52467-04-0
PubChem CID
9547069
Canonical SMILES
CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)O
Isomeric SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O
InChI
InChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1
InChIKey
YVYMBNSKXOXSKW-HXUWFJFHSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
30
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.95
H-bond donors
3
H-bond acceptors
7 computed here · PubChem 8
Rotatable bonds
22 computed here · PubChem 23
TPSA (Ų)
128.3 computed here · PubChem 128
Formal charge
0
XLogP3
2.4 PubChem
Complexity
451 PubChem
Stereocenters
1 defined, 1 undefinedCIP: C20: R · P24: undefined
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C55.61%
  • H9.78%
  • N3.09%
  • O24.69%
  • P6.83%

Isotope pattern

100%453.28624%454.2894.2%455.291456.294

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
4.46 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-4.01 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.24 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 453.56
  • log P ≤ 5 (Crippen): 4.46
  • H-bond donors ≤ 5: 3
  • H-bond acceptors ≤ 10: 7

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Molport, Debye Scientific Co., Ltd, RR Scientific.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  4. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  5. ·Literature on PubChem

Data last updated 2026-10-14.