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
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
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
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.