Structure Database (LMSD)
Common Name
1-(2-methoxy-6Z-octadecenyl)-sn-glycero-3-phosphoserine
Systematic Name
1-(2-methoxy-6Z-octadecenyl)-sn-glycero-3-phosphoserine
Synonyms
- PS(2-OMe-18:1(6Z)/0:0)
LM ID
LMGP03060016
Status
Active
Exact Mass
Calculate m/z
539.322322
Formula
Abbrev
Main
Classification
Category
Main Class
Sub Class
String Representations
InChiKey (Click to copy)
ZBMOVTXRLZMVEF-WZVZHPRESA-N
InChi (Click to copy)
InChI=1S/C25H50NO9P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(32-2)20-33-18-22(27)19-34-36(30,31)35-21-24(26)25(28)29/h13-14,22-24,27H,3-12,15-21,26H2,1-2H3,(H,28,29)(H,30,31)/b14-13-/t22-,23?,24+/m1/s1
SMILES (Click to copy)
C(O)(=O)[C@@]([H])(N)COP(OC[C@]([H])(O)COCC(OC)CCC/C=C\CCCCCCCCCCC)(=O)O
References
Reference
New advances in the chemistry of methoxylated lipids. N. M. Carballeira. Progress in Lipid Research. Volume 41, Issue 6, November 2002, Pages 437-456.
https://www.sciencedirect.com/science/article/pii/S016378270200005X?via%3Dihub%3Dihub
https://www.sciencedirect.com/science/article/pii/S016378270200005X?via%3Dihub%3Dihub
Other Databases
PubChem CID
Calculated Physicochemical Properties
Heavy Atoms
36
Rings
0
Aromatic Rings
0
Rotatable Bonds
26
Van der Waals Molecular Volume
545.72
Topological Polar Surface Area
157.77
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
10
logP
6.74
Molar Refractivity
143.16
Admin
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Updated at
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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.