Structure Database (LMSD)

Common Name
As-PL(18:0/16:0)
Systematic Name
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol-3'-)5-deoxy-5-(dimethylarsinyl)-β-D-ribofuranoside
Synonyms
LM ID
LMGP14010009
Status
Active
Exact Mass
Calculate m/z
986.544069
Formula


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MDLMOL SDF CSV TSV
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Main

Classification

String Representations

InChiKey (Click to copy)
RNIHRVOZFNFHKL-WRNIJXGTSA-N
InChi (Click to copy)
InChI=1S/C47H92AsO14P/c1-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-43(50)57-38-41(61-44(51)34-32-30-28-26-24-21-18-16-14-12-10-8-6-2)39-60-63(55,56)59-37-40(49)36-58-47-46(53)45(52)42(62-47)35-48(3,4)54/h40-42,45-47,49,52-53H,5-39H2,1-4H3,(H,55,56)/t40?,41-,42-,45-,46-,47-/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(CCCCCCCCCCCCCCCCC)=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

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

Calculated Physicochemical Properties

Heavy Atoms 63
Rings 1
Aromatic Rings 0
Rotatable Bonds 46
Van der Waals Molecular Volume 968.83
Topological Polar Surface Area 206.65
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 14
logP 13.81
Molar Refractivity 252.93

Admin

Created at
8th Jul 2020
Updated at
9th Jul 2020
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.