Structure Database (LMSD)
Common Name
PA(18:0/0:0)
Systematic Name
1-octadecanoyl-sn-glycero-3-phosphate
Synonyms
- Octadecanoic acid, 2-hydroxy-3-(phosphonooxy)propyl ester, (R)-
- 1-Stearoyl-sn-glycero-3-phosphate
- 1-Stearoyl-sn-glycerol 3-phosphate
- LPA(18:0)
- LPA(18:0)
3D model of PA(18:0/0:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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String Representations
InChiKey (Click to copy)
LAYXSTYJRSVXIH-HXUWFJFHSA-N
InChi (Click to copy)
InChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)/t20-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)O)([H])(O)COC(CCCCCCCCCCCCCCCCC)=O
Other Databases
LIPIDAT ID
7280
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
0
Aromatic Rings
0
Rotatable Bonds
22
Van der Waals Molecular Volume
450.58
Topological Polar Surface Area
113.29
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
7
logP
6.46
Molar Refractivity
115.73
Admin
Created at
-
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.
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.