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Identification
YMDB IDYMDB13563
NamePC(10:0/10:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(10:0/10:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(10:0/10:0), in particular, consists of two decanoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
Synonyms
  • 1,2-Dicaprinyl-sn-glycero-3-phosphocholine betaine
  • 1,2-Didecanoyl-sn-glycero-3-phosphocholine
  • 1,2-Didecanoyl-sn-glycero-3-phosphocholine betaine
  • Didecanoyl-L-alpha-glycerophosphorylcholine
  • Didecanoyl-L-alpha-phosphatidylcholine
  • Didecanoylglycerophosphocholine
  • Didecanoyllecithin
  • Didecanoylphosphatidylcholine
  • L-Dicapryllecithin
  • L-Didecanoyllecithin
  • L-Didecanoylphosphatidylcholine
  • PC 10:0/10:0 betaine
  • Didecanoyl-L-a-glycerophosphorylcholine
  • Didecanoyl-L-α-glycerophosphorylcholine
  • Didecanoyl-L-a-phosphatidylcholine
  • Didecanoyl-L-α-phosphatidylcholine
  • DDPC CPD
CAS numberNot Available
WeightAverage: 565.729
Monoisotopic: 565.374354765
InChI KeyMLKLDGSYMHFAOC-AREMUKBSSA-N
InChIInChI=1S/C28H56NO8P/c1-6-8-10-12-14-16-18-20-27(30)34-24-26(25-36-38(32,33)35-23-22-29(3,4)5)37-28(31)21-19-17-15-13-11-9-7-2/h26H,6-25H2,1-5H3/t26-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC28H56NO8P
SMILES[H][C@@](COC(=O)CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP2.45ALOGPS
logP2.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity160.65 m³·mol⁻¹ChemAxon
Polarizability64.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ER PC(10:0/10:0)PW002780 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(10:0/10:0)PW002791 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(10:0/10:0)PW002799 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Citicoline + DG(10:0/10:0/0:0) → Cytidine monophosphate + hydron + PC(10:0/10:0)
LysoPC(10:0)PC(10:0/10:0)
PE-NMe2(10:0/10:0) + S-Adenosyl-L-methionineS-Adenosylhomocysteine + hydron + PC(10:0/10:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID78226
HMDB IDNot Available
Pubchem Compound ID16219892
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
CPT1
Uniprot ID:
P17898
Molecular weight:
44829.0
Reactions
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
General function:
Involved in N-methyltransferase activity
Specific function:
S-adenosyl-L-methionine + phospholipid olefinic fatty acid = S-adenosyl-L-homocysteine + phospholipid methylene fatty acid
Gene Name:
OPI3
Uniprot ID:
P05375
Molecular weight:
23150.09961
Reactions
S-adenosyl-L-methionine + phospholipid olefinic fatty acid → S-adenosyl-L-homocysteine + phospholipid methylene fatty acid.