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)
Main
Classification
Category
Main Class
Sub Class
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
References
Reference
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
DOI: 10.1021/jasms.0c00094
PMID: 32342697
J Am Soc Mass Spectrom. 2020
DOI: 10.1021/jasms.0c00094
PMID: 32342697
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
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.