Structure Database (LMSD)
Systematic Name
1-(9,10-Methylenehexadecanoyl)-sn-glycero-2,3-cyclic phosphate
Synonyms
- PHYLPA
3D model of
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)
GKTQBJMLXAMCPC-CTWPCTMYSA-N
InChi (Click to copy)
InChI=1S/C20H37O6P/c1-2-3-4-8-11-17-14-18(17)12-9-6-5-7-10-13-20(21)24-15-19-16-25-27(22,23)26-19/h17-19H,2-16H2,1H3,(H,22,23)/t17?,18?,19-/m1/s1
SMILES (Click to copy)
[C@]1(COP(O1)(=O)O)([H])COC(CCCCCCCC1CC1CCCCCC)=O
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Physarum polycephalum
(#5791)
Eumycetozoa
(#142796)
Inhibition of eukaryotic DNA polymerase alpha with a novel lysophosphatidic acid (PHYLPA) isolated from myxoamoebae of Physarum polycephalum,
J Biol Chem, 1992
J Biol Chem, 1992
Pubmed ID:
1400463
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
2
Aromatic Rings
Rotatable Bonds
16
Van der Waals Molecular Volume
399.77
Topological Polar Surface Area
86.20
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
6
logP
6.41
Molar Refractivity
105.64
Reactions
Filter by species:
ⓘ
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Admin
Created at
22nd May 2023
Updated at
1st Jun 2023
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.