Structure Database (LMSD)
Common Name
As-PL(16:0/0:0)
Systematic Name
1-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol-3'-)5-deoxy-5-(dimethylarsinyl)-β-D-ribofuranoside
Synonyms
- L-As-PL(16:0/0:0)
LM ID
LMGP14040001
Formula
C29H58O13PAs
Exact Mass
Calculate m/z
720.283104
Status
Curated
3D model of As-PL(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
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Undaria pinnatifida
(#74381)
Phaeophyceae
(#2870)
Arsenosugar Phospholipids (As-PL) in Edible Marine Algae: An Interplay between Liquid Chromatography with Electrospray Ionization Multistage Mass Spectrometry and Phospholipases A1 and A2 for Regiochemical Assignment.,
J Am Soc Mass Spectrom, 2020
J Am Soc Mass Spectrom, 2020
Pubmed ID:
32342697
String Representations
InChiKey (Click to copy)
PNEIVAYPPKIEGN-BUUFUZTBSA-N
InChi (Click to copy)
InChI=1S/C29H58AsO13P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(33)39-19-23(31)21-41-44(37,38)42-22-24(32)20-40-29-28(35)27(34)25(43-29)18-30(2,3)36/h23-25,27-29,31-32,34-35H,4-22H2,1-3H3,(H,37,38)/t23-,24?,25-,27-,28-,29-/m1/s1
SMILES (Click to copy)
[C@](COP(=O)(O)OCC(O)CO[C@H]1[C@H](O)[C@H](O)[C@@H](C[As](C)(=O)C)O1)([H])(O)COC(CCCCCCCCCCCCCCC)=O
Calculated Physicochemical Properties
Heavy Atoms
44
Rings
1
Aromatic Rings
0
Rotatable Bonds
28
Van der Waals Molecular Volume
651.28
Topological Polar Surface Area
200.58
Hydrogen Bond Donors
5
Hydrogen Bond Acceptors
13
logP
6.99
Molar Refractivity
169.51
Admin
Created at
9th Jul 2020
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.