Structure database (LMSD)

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LM IDLMGP13010010
Common NameCDP-DG(16:0/22:3(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-(hexadecanoyloxy)propoxy]phosphinic acid
SynonymsCDP-DG(38:3); CDP-DG(16:0_22:3)
Exact Mass
1031.5612 (neutral)    Calculate m/z:
FormulaC50H87N3O15P2
CategoryGlycerophospholipids [GP]
Main ClassCDP-Glycerols [GP13]
Sub ClassCDP-diacylglycerols [GP1301]
AbbrevCDP-DG 38:3
Abbrev ChainsCDP-DG 16:0_22:3
PubChem CID53477919
HMDB IDHMDB0006975
SWISSLIPIDS IDSLM:000741529
InChIKeyPRJKJLIDAWKOGK-ISWZWBLASA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C50H87N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h11,13,17-18,20-21,37-38,42-43,47-49,56-57H,3-10,12,14-16,19,22-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b13-11-,18-17-,21-20-/t42-,43-,47+,48?,49-/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)CCCCCCCCCCCCCCC
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StatusActive
Calculated physicochemical properties (?):
 Heavy Atoms70Rings2Aromatic Rings1Rotatable Bonds45
 van der Waals
Molecular Volume
1021.33Topological Polar
Surface Area
267.56Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
17
 logP14.02Molar
Refractivity
273.71    
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.