Structure Database (LMSD)

Common Name
As-PL(20:0/18:0)
Systematic Name
1-eicosanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-glycerol-3'-)5-deoxy-5-(dimethylarsinyl)-β-D-ribofuranoside
Synonyms
LM ID
LMGP14010012
Formula
C51H100O14PAs
Exact Mass
Calculate m/z
1042.606669
Status
Active

Classification

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
Pubmed ID: 32342697

String Representations

InChiKey (Click to copy)
HHIDMRZKJSSPIC-XTUVEDISSA-N
InChi (Click to copy)
InChI=1S/C51H100AsO14P/c1-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-47(54)61-42-45(65-48(55)38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-2)43-64-67(59,60)63-41-44(53)40-62-51-50(57)49(56)46(66-51)39-52(3,4)58/h44-46,49-51,53,56-57H,5-43H2,1-4H3,(H,59,60)/t44?,45-,46-,49-,50-,51-/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(CCCCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCCCC)=O

Calculated Physicochemical Properties

Heavy Atoms 67
Rings 1
Aromatic Rings 0
Rotatable Bonds 50
Van der Waals Molecular Volume 1038.03
Topological Polar Surface Area 206.65
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 14
logP 15.37
Molar Refractivity 271.40

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.