Showing metabocard for PS(18:0/18:2(9Z,12Z)) (BMDB0012380)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:16 UTC
Update Date2020-05-21 16:28:19 UTC
BMDB IDBMDB0012380
Secondary Accession Numbers
  • BMDB12380
Metabolite Identification
Common NamePS(18:0/18:2(9Z,12Z))
DescriptionPS(18:0/18:2(9Z,12Z)), also known as PS(18:0/18:2) or pSer(36:2), 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(18:0/18:2(9Z,12Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:0/18:2(9Z,12Z)) can be biosynthesized from PC(18:0/18:2(9Z,12Z)) and L-serine through its interaction with the enzyme phosphatidylserine synthase. Furthermore, PS(18:0/18:2(9Z,12Z)) can be converted into PE(18:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(18:0/18:2(9Z,12Z)) can be converted into PE(18:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:0/18:2(9Z,12Z)) pathway and phosphatidylcholine biosynthesis PC(18:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-L-serineChEBI
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoserineChEBI
1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphoserineChEBI
Phosphatidylserine(18:0/18:2)ChEBI
Phosphatidylserine(18:0/18:2n6)ChEBI
Phosphatidylserine(18:0/18:2W6)ChEBI
PS(18:0/18:2)ChEBI
PS(18:0/18:2N6)ChEBI
pSer(18:0/18:2)ChEBI
pSer(18:0/18:2n6)ChEBI
pSer(18:0/18:2W6)ChEBI
pSer(36:2)ChEBI
Phosphatidylserine(36:2)HMDB
PS(18:0/18:2W6)HMDB
PS(36:2)HMDB
PS(18:0/18:2(9Z,12Z))Lipid Annotator
1-Stearoyl-2-linoleoyl-GPSHMDB
Phosphatidylserine(18:0/18:2(9Z,12Z))HMDB
Pser(18:0/18:2(9Z,12Z))HMDB
Chemical FormulaC42H78NO10P
Average Molecular Weight788.0432
Monoisotopic Molecular Weight787.536334233
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy((2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H78NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,38-39H,3-11,13,15-17,19,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b14-12-,20-18-/t38-,39+/m1/s1
InChI KeyAGTPCXBHIGMTEU-NREGDSCDSA-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
logP4.97ALOGPS
logP10.55ChemAxon
logS-7ALOGPS
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 Count42ChemAxon
Refractivity217.47 m³·mol⁻¹ChemAxon
Polarizability93.52 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-9030020400-35fdc502a0c5332d80bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9020000000-6e39fb542c07d3f7f70aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9033011100-8e765ae1c978794e0a1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-1190021200-cc18197b14e3a7318b10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5290010000-2cba48fff257e2b3d121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9130000000-5fbab6d31a1f06ef3f89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000004900-ef7e44d1be3adfa5a09dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0400004900-31bf8f1446ce1d1b222fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0400004900-31bf8f1446ce1d1b222fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-5dedc46c40b917f10744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0002059500-fc569869be28f3940fd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0002059100-44bc5c73d7a48a8f8fb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-a24428b88fc31234d1d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000001900-9c4fec99b40594066f80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017s-0070905300-7b5d83873dd2a79e2296View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0000001690-430793a1f49553bdd03eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000290-2af557577adf8dd4d0b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-ad089ba119dae26a0d13View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
  • Placenta
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
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0012380
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028997
KNApSAcK IDNot Available
Chemspider ID7826041
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547091
PDB IDNot Available
ChEBI ID84513
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(18:0/18:2(9Z,12Z)) → PE(18:0/18:2(9Z,12Z)) + 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(18:0/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:0/18:2(9Z,12Z))details