Structure Database (LMSD)
Common Name
PA(O-18:0/0:0)
Systematic Name
1-octadecyl-glycero-3-phosphate
Synonyms
- PA(O-18:0)
- PA(O-18:0_0:0)
LM ID
LMGP10060004
Formula
Exact Mass
Calculate m/z
424.295378
Sum Composition
Abbrev Chains
PA O-18:0_0:0
Status
Computationally Generated
3D model of PA(O-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
Biological Context
1-Octadecyl-2-hydroxy-sn-glycero-3-phosphate (1-Octadecyl LPA) is a LPA analog containing stearic acid at the sn-1 position. LPA binds to one of five different G protein linked receptors to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility.1,2 Alkyl ether-linked LPA derivatives have a higher platelet aggregating activity than the acyl derivatives, most likely stemming from an alkyl-specific LPA receptor. For example, 1-octadecyl LPA has a platelet aggregating EC50 value of 9 nM versus 1-octadecanoyl LPA which has an EC50 value of 177 nM.3
This information has been provided by Cayman Chemical
References
1. Tokumura, A., Sinomiya, J., Kishimoto, S., et al. Human platelets respond differentially to lysophosphatidic acids having a highly unsaturated fatty acyl group and alkyl ether-linked lysophosphatidic acids. Biochem. J. 365(Pt 3), 617-628 (2002).
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).
3. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol. 4(6), 213-219 (1994).
Reactions
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String Representations
InChiKey (Click to copy)
HUUYDUFSUADEJQ-OAQYLSRUSA-N
InChi (Click to copy)
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)O)([H])(O)COCCCCCCCCCCCCCCCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
0
Aromatic Rings
0
Rotatable Bonds
22
Van der Waals Molecular Volume
444.43
Topological Polar Surface Area
96.22
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
7.22
Molar Refractivity
116.08
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.