Showing metabocard for PS(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (BMDB0012437)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:30 UTC
Update Date2020-05-11 20:27:05 UTC
BMDB IDBMDB0012437
Secondary Accession Numbers
  • BMDB12437
Metabolite Identification
Common NamePS(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z))
DescriptionPS(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. 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. PS(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl chain to the C-1 atom, and one 8Z,11Z,14Z-eicosatrienoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidonoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Arachidonoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(20:4/20:3)HMDB
Phosphatidylserine(20:4n6/20:3n6)HMDB
Phosphatidylserine(20:4W6/20:3W6)HMDB
Phosphatidylserine(40:7)HMDB
PS(20:4/20:3)HMDB
PS(20:4N6/20:3N6)HMDB
PS(20:4W6/20:3W6)HMDB
PS(40:7)HMDB
pSer(20:4/20:3)HMDB
pSer(20:4n6/20:3n6)HMDB
pSer(20:4W6/20:3W6)HMDB
pSer(40:7)HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC46H76NO10P
Average Molecular Weight834.0701
Monoisotopic Molecular Weight833.520684169
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxyphosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)C(O)=O
InChI Identifier
InChI=1S/C46H76NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29,31,42-43H,3-10,15-16,21-22,27-28,30,32-41,47H2,1-2H3,(H,50,51)(H,52,53)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-/t42-,43+/m1/s1
InChI KeyIEHVRLNIHFLLMS-WUDDRQCASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. 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 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
Alternative Parents
Substituents
  • Diacyl-glycerol-3-phosphoserine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.08ALOGPS
logP10.52ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.68 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity241.46 m³·mol⁻¹ChemAxon
Polarizability95.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9031020120-178f789cedb68c140665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000100-ac97dbfa3c3f38862852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9044003100-9fea55a592f1738bd46aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uei-3269050450-501a53fb9c8c4f08c0a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-9458120110-cfc75aeacb857e9d022dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9101100000-4b71af03da067de4ea10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0000001690-8d2385908a17cebc7231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000290-033e08ce22c2b76afa86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-c26ebb5554ddb08b6af6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udq-0000009990-1cf5cfd563e0f474a421View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6y-0900009990-9ed5931b8edefa2dc2b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-0900009990-9ed5931b8edefa2dc2b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000001090-1c258fb5990a6a71e761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0003069160-4aece330a2ac822147c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003069110-52ff4b71cf609f4c7b35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-081dfffa68f609567a18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000190-6c1a79d627ed8b3e57faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pcd-0007900530-3be68c6535180af65f94View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
HeartExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0012437
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029053
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925751
PDB IDNot Available
ChEBI ID88531
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available