Structure Database (LMSD)
Common Name
PA(16:0/0:0)
Systematic Name
1-hexadecanoyl-sn-glycero-3-phosphate
Synonyms
- Hexadecanoic acid, 2-hydroxy-3-(phosphonooxy)propyl ester, (R)-
- Palmitin, 1-mono-, 3-(dihydrogen phosphate), L-
- 1-Palmitoyl-sn-glycerol 3-phosphate
- 1-Palmitoyl-sn-glyceryl 3-phosphate
- LPA(16:0)
- LPA(16:0)
3D model of PA(16:0/0:0)
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
Biological Context
1-Palmitoyl-2-hydroxy-sn-glycero-3-PA (1-Palmitoyl LPA) is a LPA analog containing palmitic acid at the sn-1 position. LPA binds to one of at least five different G protein-coupled receptors to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility.1,2 Additionally, 1-palmitoyl LPA enhances the action of β-lactam antibiotics (ampicillin, piperacillin, and ceftazidime) on various strains of P. aeruginosa, a pathogen associated with pulmonary disease and pneumonia, via binding both Ca2+ and Mg2+.3
This information has been provided by Cayman Chemical
References
3. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol. 4(6), 213-219 (1994).
2. Noguchi, K., Ishii, S., and Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J. Biol. Chem. 278(28), 25600-25606 (2003).
Reactions
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String Representations
InChiKey (Click to copy)
YNDYKPRNFWPPFU-GOSISDBHSA-N
InChi (Click to copy)
InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)/t18-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)O)([H])(O)COC(CCCCCCCCCCCCCCC)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
20
Van der Waals Molecular Volume
415.98
Topological Polar Surface Area
113.29
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
7
logP
5.68
Molar Refractivity
106.49
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.