Structure database (LMSD)

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LM IDLMGP00000067
Common NamePT(20:1(9Z)/20:4(5Z,8Z,11Z,14Z))
Systematic Name1-(9Z-eicosenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-
phosphothreonine
SynonymsPT(20:1/20:4)
Exact Mass
851.5676 (neutral)    Calculate m/z:
FormulaC47H82NO10P
CategoryGlycerophospholipids [GP]
Main ClassOther Glycerophospholipids [GP00]
Sub Class-
PubChem CID-
InChIKeyAOPDJXXVYGUFIR-SCRBSXKESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C47H82NO10P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-44(49)55-40-43(41-56-59(53,54)58-42(3)46(48)47(51)52)57-45(50)39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h13,15,19,21-22,24-25,27,31,33,42-43,46H,4-12,14,16-18,20,23,26,28-30,32,34-41,48H2,1-3H3,(H,51,52)(H,53,54)/b15-13-,21-19-,24-22-,27-25-,33-31-/t42-,43-,46+/m1/s1
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SMILES
C(O)(=O)[C@@]([H])(N)[C@@H](C)OP(OC[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCCCC)=O)(=O)O
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StatusActive
ReferencesPhosphatidylthreonine and Lipid-Mediated Control of Parasite Virulence
DOI:10.1371/journal.pbio.1002288
Toxoplasma gondii
Calculated physicochemical properties (?):
 Heavy Atoms59Rings0Aromatic Rings0Rotatable Bonds43
 van der Waals
Molecular Volume
919.27Topological Polar
Surface Area
171.68Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
11
 logP13.94Molar
Refractivity
242.24    
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.