Showing metabocard for PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) (BMDB0012404)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:50 UTC
Update Date2020-05-21 16:28:21 UTC
BMDB IDBMDB0012404
Secondary Accession Numbers
  • BMDB12404
Metabolite Identification
Common NamePS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))
DescriptionPS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)), also known as ps(18:2(9z,12z)/20:3(8z,11z,14z)) or PS(18:2/20:3), 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(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) and L-serine through the action of the enzyme phosphatidylserine synthase. Furthermore, PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) can be converted into PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) through the action of the enzyme phosphatidylserine decarboxylase. Finally, PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) can be converted into PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Linoleoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:2/20:3)HMDB
Phosphatidylserine(18:2n6/20:3n6)HMDB
Phosphatidylserine(18:2W6/20:3W6)HMDB
Phosphatidylserine(38:5)HMDB
PS(18:2/20:3)HMDB
PS(18:2N6/20:3N6)HMDB
PS(18:2W6/20:3W6)HMDB
PS(38:5)HMDB
pSer(18:2/20:3)HMDB
pSer(18:2n6/20:3n6)HMDB
pSer(18:2W6/20:3W6)HMDB
pSer(38:5)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC44H76NO10P
Average Molecular Weight810.0487
Monoisotopic Molecular Weight809.520684169
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(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)CCCCCCC\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/C44H76NO10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,40-41H,3-10,15-16,20,23,25-39,45H2,1-2H3,(H,48,49)(H,50,51)/b13-11-,14-12-,19-17-,21-18-,24-22-/t40-,41+/m1/s1
InChI KeyMGPMTJBAWDIKQN-GIVBSXOZSA-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
Polarizability93.92 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, Positivesplash10-000l-9040010310-ed3af85c5716d3ad1a43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000100-f106a221822efc176975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9053003100-7a7be143cb041ab39748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0c29-2192020220-405d97597712542bf17dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5290110100-d2ca17b8a9253f6a00feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-a9c07bd3fbcbc0ff6931View 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
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
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 IDHMDB0012404
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029020
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925469
PDB IDNot Available
ChEBI ID88491
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(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) → PE(18:2(9Z,12Z)/20:3(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(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))details