CDP-DG(14:0/19:1(9Z)) (PAMDB003736)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003736
Identification
Name: CDP-DG(14:0/19:1(9Z))
Description:CDP-DG(14:0/19:1(9Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. CDP-DG(14:0/19:1(9Z)), in particular, consists of one tetradecanoyl chain to C-1 atom, and one 9Z-nonadecenoyl to the C-2 atom. In Pseudomonas aeruginosa glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(14:0/19:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-myristoyl-2-9Z-nonadecenoyl-sn-glycero-3-cytidine-5'-diphosphate
  • 1-Myristoyl-2-9Z-nonadecenoyl-sn-glycero-3-cytidine-5'-diphosphoric acid
  • 1-tetradecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-CDP
  • 1-tetradecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate
  • 1-Tetradecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid
  • CDP-DG(14:0/19:1)
  • CDP-DG(33:1)
  • CDP-Diacylglycerol(14:0/19:1)
  • CDP-Diacylglycerol(33:1)
Chemical Formula: C45H81N3O15P2
Average Molecular Weight: 966.097
Monoisotopic Molecular Weight: 965.514292916
InChI Key: NVPKIIXWHNEIQG-XNIKWMRVSA-N
InChI:InChI=1S/C45H81N3O15P2/c1-3-5-7-9-11-13-15-16-17-18-19-21-23-25-27-29-31-41(50)61-37(34-58-40(49)30-28-26-24-22-20-14-12-10-8-6-4-2)35-59-64(54,55)63-65(56,57)60-36-38-42(51)43(52)44(62-38)48-33-32-39(46)47-45(48)53/h17-18,32-33,37-38,42-44,51-52H,3-16,19-31,34-36H2,1-2H3,(H,54,55)(H,56,57)(H2,46,47,53)/b18-17-/t37-,38-,42+,43?,44-/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid
Traditional IUPAC Name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00583 mg/mLALOGPS
logP6.29ALOGPS
logP9.64ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area263.27 Å2ChemAxon
Rotatable Bond Count42ChemAxon
Refractivity245.93 m3·mol-1ChemAxon
Polarizability104.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
DG(14:0/19:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(14:0/19:1(9Z)) + Pyrophosphate
CDP-DG(14:0/19:1(9Z)) + L-Serine + L-Serine > PS(14:0(3-OH)/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
CDP-DG(14:0/19:1(9Z)) + L-Serine + L-Serine > PS(14:0(3-OH)/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
Pathways:
Spectra
Spectra:
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• Phosphatidate cytidylyltransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
CTP + phosphatidate = diphosphate + CDP- diacylglycerol
Gene Name:
cdsA
Locus Tag:
PA3651
Molecular weight:
28.9 kDa
Reactions
CTP + phosphatidate = diphosphate + CDP-diacylglycerol.
Protein Details
• CDP-diacylglycerol--serine O-phosphatidyltransferase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
Gene Name:
pssA
Locus Tag:
PA4693
Molecular weight:
29.3 kDa
Reactions
CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine.

Transporters

Protein Details
• Probable phospholipid ABC transporter permease protein mlaE
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Locus Tag:
PA4455
Molecular weight:
28.4 kDa