Showing metabocard for PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0012362)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:36:55 UTC
Update Date2020-05-21 16:28:18 UTC
BMDB IDBMDB0012362
Secondary Accession Numbers
  • BMDB12362
Metabolite Identification
Common NamePS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as ps(16:0/22:6(4z,7z,10z,13z,16z,19z)) or PS(16:0/22:6), 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(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoserine lipid molecule. PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and L-serine through the action of the enzyme phosphatidylserine synthase. Furthermore, PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. Finally, PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserineChEBI
Phosphatidylserine(16:0/22:6)ChEBI
Phosphatidylserine(16:0/22:6n3)ChEBI
Phosphatidylserine(16:0/22:6W3)ChEBI
Phosphatidylserine(38:6)ChEBI
PS(16:0/22:6)ChEBI
PS(16:0/22:6N3)ChEBI
PS(16:0/22:6W3)ChEBI
PS(38:6)ChEBI
pSer(16:0/22:6)ChEBI
pSer(16:0/22:6n3)ChEBI
pSer(16:0/22:6W3)ChEBI
pSer(38:6)ChEBI
1-Palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphoserineHMDB
1-Hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoserineHMDB
PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC44H74NO10P
Average Molecular Weight808.0328
Monoisotopic Molecular Weight807.505034105
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(hexadecanoyloxy)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-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)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/C44H74NO10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-43(47)55-40(38-53-56(50,51)54-39-41(45)44(48)49)37-52-42(46)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24,26,30,32,40-41H,3-4,6,8-10,12,14-16,19,22-23,25,27-29,31,33-39,45H2,1-2H3,(H,48,49)(H,50,51)/b7-5-,13-11-,18-17-,21-20-,26-24-,32-30-/t40-,41+/m1/s1
InChI KeyPWBBJQOVCTWPIM-FAYDGCQZSA-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
logP5.01ALOGPS
logP9.99ChemAxon
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
Refractivity231.14 m³·mol⁻¹ChemAxon
Polarizability91.88 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-9022100300-2018ffbabd0dd47e4fadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010000100-fe0e9b19faa8666b38a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9152002000-dcf56d3e35f50a37c3f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-2193200320-de9c48168f3b7748e1aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-5291100100-1fb3dc5dac10ea53a3c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9021000000-47b16e29cf071f5e8007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-0000001690-8904c54a778b83af24f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000290-78e12fb7fbaa4252f464View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-cb8029e6c627bf17291bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000001090-db2758fb9ca0acf15406View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0003339160-3447e4b237a4d29816c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0003339110-a3684d078cc957ef66e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-7d51a5978beb6b9ecff3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000190-58576aa95dc312ff8e4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0149600640-20785e5f0c8a03cb5f25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03vi-0000009990-ab20a1af9c152e58b2c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03vo-0900009990-abd3825685d973162d33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03vo-0900009990-abd3825685d973162d33View 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 IDHMDB0012362
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028980
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46891805
PDB IDNot Available
ChEBI ID79103
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(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) → PE(16:0/22:6(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(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details