Showing metabocard for PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0012406)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:53 UTC
Update Date2020-05-21 16:28:21 UTC
BMDB IDBMDB0012406
Secondary Accession Numbers
  • BMDB12406
Metabolite Identification
Common NamePS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as ps(18:2(9z,12z)/22:6(4z,7z,10z,13z,16z,19z)) or PS(18:2/22:6), 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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and L-serine through the action of the enzyme phosphatidylserine synthase. Furthermore, PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:2/22:6)HMDB
Phosphatidylserine(18:2n6/22:6n3)HMDB
Phosphatidylserine(18:2W6/22:6W3)HMDB
Phosphatidylserine(40:8)HMDB
PS(18:2/22:6)HMDB
PS(18:2N6/22:6N3)HMDB
PS(18:2W6/22:6W3)HMDB
PS(40:8)HMDB
pSer(18:2/22:6)HMDB
pSer(18:2n6/22:6n3)HMDB
pSer(18:2W6/22:6W3)HMDB
pSer(40:8)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC46H74NO10P
Average Molecular Weight832.0542
Monoisotopic Molecular Weight831.505034105
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O
InChI Identifier
InChI=1S/C46H74NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-45(49)57-42(40-55-58(52,53)56-41-43(47)46(50)51)39-54-44(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,32,34,42-43H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t42-,43+/m1/s1
InChI KeyUKKRKBLKOFZCGO-NJNSWFATSA-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
logP10.15ChemAxon
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 Count40ChemAxon
Refractivity242.57 m³·mol⁻¹ChemAxon
Polarizability93.57 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, Positivesplash10-0uxr-0000001690-f6727ce19f5178aed3d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000290-6557cbd455f7fe96e1f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-e58b572d99ed412a9474View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-73b6d0ec5c277fb09d84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000190-2e4f53efa456f7e87f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ec-0033900530-9d2057b3cb2782e6261eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000001090-5f1f821439c4001ba23bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0003069160-3d5dbe93e5f0382b1546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003069110-4f4b3dd7a92bc0029776View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue2-0000009990-b9da579747a1872f03f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue8-0900009990-8a1faea889fd8edfd0ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue8-0900009990-8a1faea889fd8edfd0ceView 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 IDHMDB0012406
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029022
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926085
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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) → PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + 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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details