Showing metabocard for PS(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)) (BMDB0012424)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:14 UTC
Update Date2020-05-11 20:26:54 UTC
BMDB IDBMDB0012424
Secondary Accession Numbers
  • BMDB12424
Metabolite Identification
Common NamePS(20:3(8Z,11Z,14Z)/18:2(9Z,12Z))
DescriptionPS(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)) 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(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)), in particular, consists of one 8Z,11Z,14Z-eicosatrienoyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl 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-Homo-g-linolenoyl-2-linoleoyl-sn-glycero-3-phosphoserineHMDB
1-Homo-gamma-linolenoyl-2-linoleoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(20:3/18:2)HMDB
Phosphatidylserine(20:3n6/18:2n6)HMDB
Phosphatidylserine(20:3W6/18:2W6)HMDB
Phosphatidylserine(38:5)HMDB
PS(20:3/18:2)HMDB
PS(20:3N6/18:2N6)HMDB
PS(20:3W6/18:2W6)HMDB
PS(38:5)HMDB
pSer(20:3/18:2)HMDB
pSer(20:3n6/18:2n6)HMDB
pSer(20:3W6/18:2W6)HMDB
pSer(38:5)HMDB
1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoserineHMDB
PS(20:3(8Z,11Z,14Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC44H76NO10P
Average Molecular Weight810.0487
Monoisotopic Molecular Weight809.520684169
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)C(O)=O
InChI Identifier
InChI=1S/C44H76NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-42(46)52-37-40(38-53-56(50,51)54-39-41(45)44(48)49)55-43(47)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,40-41H,3-10,15-16,20,24-39,45H2,1-2H3,(H,48,49)(H,50,51)/b13-11-,14-12-,19-17-,21-18-,23-22-/t40-,41+/m1/s1
InChI KeyKUGZOCKMPSWEGI-CCWDTQCASA-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
logP5ALOGPS
logP10.35ChemAxon
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
Refractivity230.02 m³·mol⁻¹ChemAxon
Polarizability93.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pc-9040010300-ce23ac59d1cfbad5ff06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000100-83e4ebe864c10b6d0c9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9043003100-1032721246ce4f413f66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-2195030320-e4e34addb1d0a76342cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-9487120200-318f7f91e0531f5f6c22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9111000000-d456e5b62408fb2b70a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0000001690-4fa3608cd949269688abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000290-6b936c9e107ff3bc5aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-6d460281a4d0df78ca52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-b2a8be4885f9acfe9c2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000190-d931a25d63f7a546300fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-0033900530-c7bccb9be1253e270d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-0e4440747f008722b23eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0003069160-27dfd01cb7ad4ac791e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003069110-d593dc2b979f9c2340c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0000009990-91065fa06ae51500cde9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ou-0900009990-e136b0b2a0529029b72aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-0900009990-e136b0b2a0529029b72aView 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 IDHMDB0012424
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029040
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925712
PDB IDNot Available
ChEBI ID88521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available