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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-09 06:33:47 UTC

Update Date

2022-11-30 19:26:25 UTC

HMDB ID

HMDB0115963

Secondary Accession Numbers

None

Metabolite Identification

Common Name

CDP-DG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))

Description

CDP-DG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of clupanodonic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids).

Structure

MOL SDF PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅₂H₈₅N₃O₁₅P₂

Average Molecular Weight

1054.206

Monoisotopic Molecular Weight

1053.545593045

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C52H85N3O15P2/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/h5,7,11,13,17-19,21-23,26,28,39-40,44-45,49-51,58-59H,3-4,6,8-10,12,14-16,20,24-25,27,29-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b7-5-,13-11-,19-17-,22-21-,23-18-,28-26-/t44-,45-,49+,50?,51-/m1/s1

InChI Key

GIJPZUZBMLGTJD-LXCVQGDLSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Endogenous (HMDB: HMDB0115963)

Process

Naturally occurring process

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Predicted Molecular Properties

Not Available

Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.0 minutes	32390414
Predicted by Siyang on May 30, 2022	28.8049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5438.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	176.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	334.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	922.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1657.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1135.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	311.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2992.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1318.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2599.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1152.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	696.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	230.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	293.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.9 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available
Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))		Not Available