Structure database (LMSD)

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LM IDLMGP04040002
Common Name-
Systematic Name1-(6-[5]-ladderane-hexanyl)-2-(8-[3]-ladderane-octanyl)-sn-glycero-3-phospho-
(1'-sn-glycerol)
Synonyms-
Exact Mass
760.5043 (neutral)    Calculate m/z:
FormulaC44H73O8P
CategoryGlycerophospholipids [GP]
Main ClassGlycerophosphoglycerols [GP04]
Sub ClassDialkylglycerophosphoglycerols [GP0404]
AbbrevPG dO-38:9
PubChem CID42607476
InChIKeyUMADEKBFSHQMRM-ODWHZCLLSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C44H73O8P/c45-23-29(46)24-51-53(47,48)52-26-30(25-49-19-9-6-4-8-12-28-22-37-38(28)44-42-34-18-17-33(34)41(42)43(37)44)50-20-10-5-2-1-3-7-11-27-13-14-35-36(21-27)40-32-16-15-31(32)39(35)40/h27-46H,1-26H2,(H,47,48)/t27?,28?,29-,30+,31?,32?,33?,34?,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?/m0/s1
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SMILES
C(CCCCCOC[C@@](OCCCCCCCCC1CC2C3C4CCC4C3C2CC1)(COP(=O)(O)OC[C@@]([H])(O)CO)[H])C1CC2C3C4C5CCC5C4C3C21
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StatusActive
CommentsSubmitted by Henry Boumann, Netherlands
ReferencesPubMed ID: 18385981
Calculated physicochemical properties (?):
 Heavy Atoms53Rings9Aromatic Rings0Rotatable Bonds26
 van der Waals
Molecular Volume
748.67Topological Polar
Surface Area
114.68Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
8
 logP11.11Molar
Refractivity
207.39    
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.