Showing metabocard for PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (BMDB0012403)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:49 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0012403
Secondary Accession Numbers
  • BMDB12403
Metabolite Identification
Common NamePS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))
DescriptionPS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)), also known as ps(18:2(9z,12z)/18:3(9z,12z,15z)) or PS(18:2/18:3), 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)/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) can be biosynthesized from PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. Furthermore, PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) can be converted into PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) can be converted into PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) pathway and phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-a-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Linoleoyl-2-alpha-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:2/18:3)HMDB
Phosphatidylserine(18:2n6/18:3n3)HMDB
Phosphatidylserine(18:2W6/18:3W3)HMDB
Phosphatidylserine(36:5)HMDB
PS(18:2/18:3)HMDB
PS(18:2N6/18:3N3)HMDB
PS(18:2W6/18:3W3)HMDB
PS(36:5)HMDB
pSer(18:2/18:3)HMDB
pSer(18:2n6/18:3n3)HMDB
pSer(18:2W6/18:3W3)HMDB
pSer(36:5)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC42H72NO10P
Average Molecular Weight781.9955
Monoisotopic Molecular Weight781.489384041
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-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)CCCCCCC\C=C/C\C=C/C\C=C/CC)C(O)=O
InChI Identifier
InChI=1S/C42H72NO10P/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/h6,8,11-14,17-20,38-39H,3-5,7,9-10,15-16,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b8-6-,13-11-,14-12-,19-17-,20-18-/t38-,39+/m1/s1
InChI KeyBUZGPRVYXXZJOM-LCWFRSHRSA-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
logP4.68ALOGPS
logP9.46ChemAxon
logS-6.9ALOGPS
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 Count39ChemAxon
Refractivity220.82 m³·mol⁻¹ChemAxon
Polarizability89.69 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-ba2bf8e0e31b33d34994View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-a7eafedf5d6d7e015346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ec-0070905300-604ffdaad7ee4f59c481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000010690-bc5ad28d7645e51fafb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000290-7a0eba3babb6d809fb99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090011310-5511144d05e4db94e409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue2-0000040900-38b9b118af6d3c71692cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue8-0400040900-bca20b0089dd61ff2f98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue8-0400040900-bca20b0089dd61ff2f98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000010900-0517d572f6aa29e4fc04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0001090300-e4609be6750cc99deb90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001090000-18a831d055f389ec07b4View 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 IDHMDB0012403
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029019
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925462
PDB IDNot Available
ChEBI IDNot Available
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)/18:3(9Z,12Z,15Z)) → PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) + 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)/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))details