Showing metabocard for PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0012395)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:37 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0012395
Secondary Accession Numbers
  • BMDB12395
Metabolite Identification
Common NamePS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as ps(18:1(9z)/22:6(4z,7z,10z,13z,16z,19z)) or PS(18:1/22:6), 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(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. Furthermore, PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Oleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:1/22:6)HMDB
Phosphatidylserine(18:1n9/22:6n3)HMDB
Phosphatidylserine(18:1W9/22:6W3)HMDB
Phosphatidylserine(40:7)HMDB
PS(18:1/22:6)HMDB
PS(18:1N9/22:6N3)HMDB
PS(18:1W9/22:6W3)HMDB
PS(40:7)HMDB
pSer(18:1/22:6)HMDB
pSer(18:1n9/22:6n3)HMDB
pSer(18:1W9/22:6W3)HMDB
pSer(40:7)HMDB
1-(9Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC46H76NO10P
Average Molecular Weight834.0701
Monoisotopic Molecular Weight833.520684169
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]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)-octadec-9-enoyloxy]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/CCCCCCCC)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/C46H76NO10P/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/h5,7,11,13,17-19,21-23,26,28,32,34,42-43H,3-4,6,8-10,12,14-16,20,24-25,27,29-31,33,35-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,23-18-,28-26-,34-32-/t42-,43+/m1/s1
InChI KeyFZVOBDJBRIEKPS-SXFSXRSVSA-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
logP5.13ALOGPS
logP10.52ChemAxon
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
Refractivity241.46 m³·mol⁻¹ChemAxon
Polarizability95.78 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, Positivesplash10-000i-9022010120-c7f4c548b49f9fb2f5b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9011000100-ca1622fe0242d08214d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9054002100-f4b46971db54441e53f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-2193030230-14b8d50dbecbcaa08858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-5291010000-051099f97f9a8ecaeda1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9121000000-f0e352b5092f0452d6d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udq-0000009990-1cf5cfd563e0f474a421View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6y-0900009990-9ed5931b8edefa2dc2b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-0900009990-9ed5931b8edefa2dc2b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000001090-1c258fb5990a6a71e761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0003069160-0af8d5d4d84161d0ab8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0003069110-65e6ce794f0f68a47fc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-081dfffa68f609567a18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000190-6c1a79d627ed8b3e57faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0033900530-7a1dc95892d6def1055aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0000001690-8d2385908a17cebc7231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000290-033e08ce22c2b76afa86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-c26ebb5554ddb08b6af6View 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 IDHMDB0012395
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029011
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925155
PDB IDNot Available
ChEBI ID90025
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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) → PE(18:1(9Z)/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(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details