Showing metabocard for PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0012427)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:18 UTC
Update Date2020-05-21 16:28:21 UTC
BMDB IDBMDB0012427
Secondary Accession Numbers
  • BMDB12427
Metabolite Identification
Common NamePS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)), also known as ps(20:3(8z,11z,14z)/20:4(5z,8z,11z,14z)) or PS(20:3/20:4), 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. Thus, PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphoserine lipid molecule. PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. Furthermore, PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) can be converted into PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine decarboxylase. Finally, PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) can be converted into PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Homo-g-linolenoyl-2-arachidonoyl-sn-glycero-3-phosphoserineHMDB
1-Homo-gamma-linolenoyl-2-arachidonoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(20:3/20:4)HMDB
Phosphatidylserine(20:3n6/20:4n6)HMDB
Phosphatidylserine(20:3W6/20:4W6)HMDB
Phosphatidylserine(40:7)HMDB
PS(20:3/20:4)HMDB
PS(20:3N6/20:4N6)HMDB
PS(20:3W6/20:4W6)HMDB
PS(40:7)HMDB
pSer(20:3/20:4)HMDB
pSer(20:3n6/20:4n6)HMDB
pSer(20:3W6/20:4W6)HMDB
pSer(40:7)HMDB
1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineHMDB
PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC46H76NO10P
Average Molecular Weight834.0701
Monoisotopic Molecular Weight833.520684169
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\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/h11-14,17-20,23-26,30,32,42-43H,3-10,15-16,21-22,27-29,31,33-41,47H2,1-2H3,(H,50,51)(H,52,53)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,32-30-/t42-,43+/m1/s1
InChI KeyQIELVOPMFCPTPX-RTYIZSBCSA-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
logP5.09ALOGPS
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
Polarizability95.36 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-9020020120-9204803208fde854f3e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010000100-9af6fd12ff6c0fb9d4cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9024003100-16939c416060953bdf29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5i-3269050350-8b4b3656df4ef76287daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-9457220110-7648d7515a389e9830d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9101100000-1afa423aa884e3853453View 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, 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, 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
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
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 IDHMDB0012427
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029043
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925722
PDB IDNot Available
ChEBI ID88513
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphatidylserine decarboxylase proenzyme, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the formation of phosphatidylethanolamine (PtdEtn) from phosphatidylserine (PtdSer). Plays a central role in phospholipid metabolism and in the interorganelle trafficking of phosphatidylserine.
Gene Name:
PISD
Uniprot ID:
Q58DH2
Molecular weight:
47244.0
Reactions
PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) → PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Carbon dioxidedetails
Enzyme Details
2. Phosphatidylserine synthase 1
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))details