Structure Database (LMSD)
Common Name
PA(16:0/18:1(9Z))
Systematic Name
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate
Synonyms
- 9-Octadecenoic acid (Z)-, 1-[[(1-oxohexadecyl)oxy]methyl]-2-(phosphonooxy)ethyl ester, (R)-
- PA(16:0/18:1)
- PA(34:1)
- PA(16:0_18:1)
3D model of PA(16:0/18:1(9Z))
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
Biological Context
1-Palmitoyl-2-oleoyl-sn-glycero-3-PA (1,2-POPA) is a phospholipid containing saturated palmitic acid (16:0) and monounsaturated oleic acid (18:1) inserted at the sn-1 and sn-2 positions, respectively. It can be used in the generation of micelles, liposomes, and other types of artificial membranes.1
This information has been provided by Cayman Chemical
References
1. Mansour, H.M., and Zografi, G. The relationship between water vapor absorption and desorption by phospholipids and bilayer phase transitions. J. Pharm. Sci. 96(2), 377-396 (2007).
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)
OPVZUEPSMJNLOM-QEJMHMKOSA-N
InChi (Click to copy)
InChI=1S/C37H71O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/b18-17-/t35-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)O)([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
LIPIDAT ID
9139
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
46
Rings
0
Aromatic Rings
0
Rotatable Bonds
37
Van der Waals Molecular Volume
730.89
Topological Polar Surface Area
119.36
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
8
logP
12.27
Molar Refractivity
189.82
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.