Showing metabocard for PS(16:1(9Z)/20:3(8Z,11Z,14Z)) (BMDB0012371)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:06 UTC
Update Date2020-05-21 16:28:19 UTC
BMDB IDBMDB0012371
Secondary Accession Numbers
  • BMDB12371
Metabolite Identification
Common NamePS(16:1(9Z)/20:3(8Z,11Z,14Z))
DescriptionPS(16:1(9Z)/20:3(8Z,11Z,14Z)), also known as ps(16:1(9z)/20:3(8z,11z,14z)) or PS(16:1/20:3), 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(16:1(9Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphoserine lipid molecule. PS(16:1(9Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(16:1(9Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from PC(16:1(9Z)/20:3(8Z,11Z,14Z)) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. Furthermore, PS(16:1(9Z)/20:3(8Z,11Z,14Z)) can be converted into PE(16:1(9Z)/20:3(8Z,11Z,14Z)) through the action of the enzyme phosphatidylserine decarboxylase. Finally, PS(16:1(9Z)/20:3(8Z,11Z,14Z)) can be converted into PE(16:1(9Z)/20:3(8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(16:1(9Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Palmitoleoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(16:1/20:3)HMDB
Phosphatidylserine(16:1n7/20:3n6)HMDB
Phosphatidylserine(16:1W7/20:3W6)HMDB
Phosphatidylserine(36:4)HMDB
PS(16:1/20:3)HMDB
PS(16:1N7/20:3N6)HMDB
PS(16:1W7/20:3W6)HMDB
PS(36:4)HMDB
pSer(16:1/20:3)HMDB
pSer(16:1n7/20:3n6)HMDB
pSer(16:1W7/20:3W6)HMDB
pSer(36:4)HMDB
1-(9Z-Hexadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(16:1(9Z)/20:3(8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC42H74NO10P
Average Molecular Weight784.0114
Monoisotopic Molecular Weight783.505034105
IUPAC Name(2S)-2-amino-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]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/CCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)C(O)=O
InChI Identifier
InChI=1S/C42H74NO10P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-41(45)53-38(36-51-54(48,49)52-37-39(43)42(46)47)35-50-40(44)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,20,22,38-39H,3-10,12,15,19,21,23-37,43H2,1-2H3,(H,46,47)(H,48,49)/b13-11-,16-14-,18-17-,22-20-/t38-,39+/m1/s1
InChI KeyKDQCUZMSFTUKER-DTHZZQGCSA-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
logP4.8ALOGPS
logP9.82ChemAxon
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
Refractivity219.7 m³·mol⁻¹ChemAxon
Polarizability91.24 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, Positivesplash10-000i-9040110400-c465b2e7d7889e5c26a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000000-ebd18bf124feab97ae5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9061010100-476c38eca850aebd75b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k9i-2192201300-ca49676dc80fa557d2c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-5291100000-bf0c93d47e7e7cf5a469View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-7cb18ed2946c8dc5a6caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udq-0000040900-0e7a4f3fdcae58803c49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6y-0400040900-5e8d61708e9836d6fb43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-0400040900-5e8d61708e9836d6fb43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2f4aa19fa103b88ee08fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-66dbd27d004f199196efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pcd-0149606400-335f00ba14c5681515e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000010900-0f4be97706923cd4a4a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0002291400-2c9f847d1175dadc80d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0002291100-6dab6d7774d61d3e0779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0000010690-5a9e0fb6c24df326a527View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000290-493620f05d7e59a6c200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090011310-c12792ef4795d12ecae6View 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 IDHMDB0012371
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028989
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925329
PDB IDNot Available
ChEBI ID90037
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(16:1(9Z)/20:3(8Z,11Z,14Z)) → PE(16:1(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(16:1(9Z)/20:3(8Z,11Z,14Z)) + L-Serine → Choline + PS(16:1(9Z)/20:3(8Z,11Z,14Z))details