Structure database (LMSD)

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LM IDLMGP13010008
Common NameCDP-DG(16:0/20:4(5Z,8Z,11Z,14Z))
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)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,
14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid
SynonymsCDP-DG(36:4); CDP-DG(16:0_20:4)
Exact Mass
1001.5143 (neutral)    Calculate m/z:
FormulaC48H81N3O15P2
CategoryGlycerophospholipids [GP]
Main ClassCDP-Glycerols [GP13]
Sub ClassCDP-diacylglycerols [GP1301]
AbbrevCDP-DG 36:4
Abbrev ChainsCDP-DG 16:0_20:4
PubChem CID53477917
HMDB IDHMDB0006973
InChIKeyGMBXECXXNMMIAN-HUOFUYQBSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C48H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-44(53)64-40(37-61-43(52)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h11,13,17-18,20,22,26,28,35-36,40-41,45-47,54-55H,3-10,12,14-16,19,21,23-25,27,29-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b13-11-,18-17-,22-20-,28-26-/t40-,41-,45+,46?,47-/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)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)COC(=O)CCCCCCCCCCCCCCC
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms68Rings2Aromatic Rings1Rotatable Bonds42
 van der Waals
Molecular Volume
984.09Topological Polar
Surface Area
267.56Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
17
 logP13.02Molar
Refractivity
264.38    
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.