Showing metabocard for PS(18:1(9Z)/20:3(8Z,11Z,14Z)) (BMDB0012393)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:35 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0012393
Secondary Accession Numbers
  • BMDB12393
Metabolite Identification
Common NamePS(18:1(9Z)/20:3(8Z,11Z,14Z))
DescriptionPS(18:1(9Z)/20:3(8Z,11Z,14Z)), also known as ps(18:1(9z)/20:3(8z,11z,14z)) or PS(18:1/20:3), 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(18:1(9Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:1(9Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:1(9Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from PC(18:1(9Z)/20:3(8Z,11Z,14Z)) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. Furthermore, PS(18:1(9Z)/20:3(8Z,11Z,14Z)) can be converted into PE(18:1(9Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(18:1(9Z)/20:3(8Z,11Z,14Z)) can be converted into PE(18:1(9Z)/20:3(8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:1(9Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:1(9Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Oleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Oleoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:1/20:3)HMDB
Phosphatidylserine(18:1n9/20:3n6)HMDB
Phosphatidylserine(18:1W9/20:3W6)HMDB
Phosphatidylserine(38:4)HMDB
PS(18:1/20:3)HMDB
PS(18:1N9/20:3N6)HMDB
PS(18:1W9/20:3W6)HMDB
PS(38:4)HMDB
pSer(18:1/20:3)HMDB
pSer(18:1n9/20:3n6)HMDB
pSer(18:1W9/20:3W6)HMDB
pSer(38:4)HMDB
1-(9Z-Octadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:1(9Z)/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC44H78NO10P
Average Molecular Weight812.0646
Monoisotopic Molecular Weight811.536334233
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)C(O)=O
InChI Identifier
InChI=1S/C44H78NO10P/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/h11,13,17-19,21-22,24,40-41H,3-10,12,14-16,20,23,25-39,45H2,1-2H3,(H,48,49)(H,50,51)/b13-11-,19-17-,21-18-,24-22-/t40-,41+/m1/s1
InChI KeyHSAQFLIHNUSBEE-LIRCASFMSA-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
logP5.11ALOGPS
logP10.71ChemAxon
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 Count42ChemAxon
Refractivity228.91 m³·mol⁻¹ChemAxon
Polarizability94.91 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-9040010310-96983c68b9123c87148bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000100-f10ba13f3189b65e5128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9053002100-be8a96ddf59d57521455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-2192020220-26ddeb83acc98a52e3f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-5290110100-73d8d8c2bf5504a80eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-a5dbe5ca1afa1e2fcbb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-573859c04b61ebf68cf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000190-714c08659686c618fcc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07pl-0033900530-17b59e49d369122c3377View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ai-0000009990-62a7de51c1e966c909d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ao-0900009990-b29b6835c098a8ad19bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ao-0900009990-b29b6835c098a8ad19bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000001090-495c42dc38341c4cc352View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0003069160-6bfce4e3e3ff9f452300View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0003069110-6485d2483371c292ba62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0000001690-39b02e092cc14f1c336dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000290-8f4f01e6565d8a5f07a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-f1c65be3b47cfe8c8092View 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 IDHMDB0012393
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029009
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925445
PDB IDNot Available
ChEBI ID90024
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(18:1(9Z)/20:3(8Z,11Z,14Z)) → PE(18:1(9Z)/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(18:1(9Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(18:1(9Z)/20:3(8Z,11Z,14Z))details