Structure Database (LMSD)
Common Name
As-PL(20:0/16:0)
Systematic Name
1-eicosanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol-3'-)5-deoxy-5-(dimethylarsinyl)-β-D-ribofuranoside
Synonyms
LM ID
LMGP14010011
Formula
C49H96O14PAs
Exact Mass
Calculate m/z
1014.575369
Status
Active
3D model of As-PL(20:0/16:0)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Main
Classification
Category
Main Class
Sub Class
String Representations
InChiKey (Click to copy)
NKTCESCCQGOPCQ-LCPNTMEESA-N
InChi (Click to copy)
InChI=1S/C49H96AsO14P/c1-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-45(52)59-40-43(63-46(53)36-34-32-30-28-26-23-18-16-14-12-10-8-6-2)41-62-65(57,58)61-39-42(51)38-60-49-48(55)47(54)44(64-49)37-50(3,4)56/h42-44,47-49,51,54-55H,5-41H2,1-4H3,(H,57,58)/t42?,43-,44-,47-,48-,49-/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])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCCCC)=O
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
Calculated Physicochemical Properties
Heavy Atoms
65
Rings
1
Aromatic Rings
0
Rotatable Bonds
48
Van der Waals Molecular Volume
1003.43
Topological Polar Surface Area
206.65
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
14
logP
14.59
Molar Refractivity
262.16
Admin
Created at
8th 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.