Showing metabocard for PS(16:1(9Z)/16:1(9Z)) (BMDB0012366)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:36:59 UTC
Update Date2020-05-21 16:28:18 UTC
BMDB IDBMDB0012366
Secondary Accession Numbers
  • BMDB12366
Metabolite Identification
Common NamePS(16:1(9Z)/16:1(9Z))
DescriptionPS(16:1(9Z)/16:1(9Z)), also known as ps(16:1(9z)/16:1(9z)) or PS(16:1/16:1), 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)/16:1(9Z)) is considered to be a glycerophosphoserine lipid molecule. PS(16:1(9Z)/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(16:1(9Z)/16:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PS(16:1(9Z)/16:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(16:1(9Z)/16:1(9Z)) can be biosynthesized from PC(16:1(9Z)/16:1(9Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. Furthermore, PS(16:1(9Z)/16:1(9Z)) can be converted into PE(16:1(9Z)/16:1(9Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. Finally, PS(16:1(9Z)/16:1(9Z)) can be converted into PE(16:1(9Z)/16:1(9Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(16:1(9Z)/16:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/16:1(9Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/16:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dipalmitoleoyl-rac-glycero-3-phosphoserineHMDB
Phosphatidylserine(16:1/16:1)HMDB
Phosphatidylserine(16:1n7/16:1n7)HMDB
Phosphatidylserine(16:1W7/16:1W7)HMDB
Phosphatidylserine(32:2)HMDB
PS(16:1/16:1)HMDB
PS(16:1N7/16:1N7)HMDB
PS(16:1W7/16:1W7)HMDB
PS(32:2)HMDB
pSer(16:1/16:1)HMDB
pSer(16:1n7/16:1n7)HMDB
pSer(16:1W7/16:1W7)HMDB
pSer(32:2)HMDB
1,2-Di(9Z-hexadecenoyl)-rac-glycero-3-phosphoserineHMDB
PS(16:1(9Z)/16:1(9Z))Lipid Annotator
Chemical FormulaC38H70NO10P
Average Molecular Weight731.949
Monoisotopic Molecular Weight731.473734456
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-2,3-bis[(9Z)-hexadec-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/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)C(O)=O
InChI Identifier
InChI=1S/C38H70NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,34-35H,3-12,17-33,39H2,1-2H3,(H,42,43)(H,44,45)/b15-13-,16-14-/t34-,35+/m1/s1
InChI KeySYAYTZJXUCQTMJ-XOZMKWGESA-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
logP4.27ALOGPS
logP8.77ChemAxon
logS-6.8ALOGPS
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 Count38ChemAxon
Refractivity199.07 m³·mol⁻¹ChemAxon
Polarizability84.82 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-9020301300-90739115dcc58bc772e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010101000-65839377ac793e1439aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9141012000-493d11698098b5ef0323View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ugu-1190302300-cb204a670520497dbffbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-5391101000-31976bf909e1aee54915View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-df8c93488a3f8b783941View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000010900-cae04fbb7cc74ec87886View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0001391600-b3165e8182707b31adafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0001391100-3950a27afa0ab9a1b302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000016900-39d23ba4b1813b1aaf2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000002900-b4094e2697a39c9ef984View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090033100-e55eb4eb6f5f2e380abaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue2-0000099900-43dc087684fecc2897ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue8-0900099900-c92245ccfbabb934c961View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue8-0900099900-c92245ccfbabb934c961View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-b8d79fe5f77511e7f343View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-59e4be9fa5befd3beb12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7x-0166109600-789538b0737e2e044e33View 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 IDHMDB0012366
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028984
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926071
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(16:1(9Z)/16:1(9Z)) → PE(16:1(9Z)/16:1(9Z)) + 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)/16:1(9Z)) + L-Serine → Choline + PS(16:1(9Z)/16:1(9Z))details