Structure database (LMSD)

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LM IDLMGP04110001
Common Name-
Systematic Name1-tetradecanoyl-2-(8-[3]-ladderane-octanyl)-sn-glycero-3-phospho-(1'-sn-
glycerol)
Synonyms-
Exact Mass
728.4992 (neutral)    Calculate m/z:
FormulaC40H73O9P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerols [GP04]
Sub Class1-acyl,2-alkylglycerophosphoglycerols [GP0411]
PubChem CID42607486
InChIKeyMWPDWUVBMJGEIM-QXIBXBCJSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C40H73O9P/c1-2-3-4-5-6-7-8-9-10-14-17-20-38(43)47-29-33(30-49-50(44,45)48-28-32(42)27-41)46-25-18-15-12-11-13-16-19-31-21-22-36-37(26-31)40-35-24-23-34(35)39(36)40/h31-37,39-42H,2-30H2,1H3,(H,44,45)/t31?,32-,33+,34?,35?,36?,37?,39?,40?/m0/s1
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SMILES
O(P(=O)(O)OC[C@@]([H])(O)CO)C[C@@](OCCCCCCCCC1CC2C3C4CCC4C3C2CC1)([H])COC(=O)CCCCCCCCCCCCC
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StatusActive
CommentsSubmitted by Henry Boumann, Netherlands
ReferencesPubMed ID: 18385981
Calculated physicochemical properties (?):
 Heavy Atoms50Rings4Aromatic Rings0Rotatable Bonds32
 van der Waals
Molecular Volume
747.42Topological Polar
Surface Area
131.75Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
9
 logP11.32Molar
Refractivity
199.77    
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.