Structure Database (LMSD)

Common Name
As-PL(14:0/16:0)
Systematic Name
1-tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol-3'-)5-deoxy-5-(dimethylarsinyl)-β-D-ribofuranoside
Synonyms
LM ID
LMGP14010006
Formula
C43H84O14PAs
Exact Mass
Calculate m/z
930.481469
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)
DXMXXIAQOFZINC-UCVOOVABSA-N
InChi (Click to copy)
InChI=1S/C43H84AsO14P/c1-5-7-9-11-13-15-17-18-20-22-24-26-28-30-40(47)57-37(34-53-39(46)29-27-25-23-21-19-16-14-12-10-8-6-2)35-56-59(51,52)55-33-36(45)32-54-43-42(49)41(48)38(58-43)31-44(3,4)50/h36-38,41-43,45,48-49H,5-35H2,1-4H3,(H,51,52)/t36?,37-,38-,41-,42-,43-/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(CCCCCCCCCCCCC)=O

Calculated Physicochemical Properties

Heavy Atoms 59
Rings 1
Aromatic Rings 0
Rotatable Bonds 42
Van der Waals Molecular Volume 899.63
Topological Polar Surface Area 206.65
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 14
logP 12.25
Molar Refractivity 234.46

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.