Structure database (LMSD)

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LM IDLMGP13010027
Common NameCDP-DG(18:1(11Z)/22:3(10Z,13Z,16Z))
Systematic Name[({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-
2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-
trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid
SynonymsCDP-DG(40:4); CDP-DG(18:1_22:3)
Exact Mass
1057.5769 (neutral)    Calculate m/z:
FormulaC52H89N3O15P2
CategoryGlycerophospholipids [GP]
Main ClassCDP-Glycerols [GP13]
Sub ClassCDP-diacylglycerols [GP1301]
AbbrevCDP-DG 40:4
Abbrev ChainsCDP-DG 18:1_22:3
PubChem CID53477936
HMDB IDHMDB0006993
SWISSLIPIDS IDSLM:000742113
InChIKeyYXFWEZRPMYWBJO-QEVNKONESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C52H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h11,13-14,16-17,19,21-22,39-40,44-45,49-51,58-59H,3-10,12,15,18,20,23-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b13-11-,16-14-,19-17-,22-21-/t44-,45-,49+,50?,51-/m1/s1
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SMILES
C(OP(=O)(OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)C(O)[C@H]1O)O)O)[C@]([H])(OC(=O)CCCCCCCC/C=C\C/C=C\C/C=C\CCCCC)COC(=O)CCCCCCCCC/C=C\CCCCCC
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms72Rings2Aromatic Rings1Rotatable Bonds46
 van der Waals
Molecular Volume
1053.29Topological Polar
Surface Area
267.56Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
17
 logP14.58Molar
Refractivity
282.85    
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.