Showing metabocard for PS(16:0/18:0) (BMDB0012356)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:36:48 UTC
Update Date2020-05-21 16:28:18 UTC
BMDB IDBMDB0012356
Secondary Accession Numbers
  • BMDB12356
Metabolite Identification
Common NamePS(16:0/18:0)
DescriptionPS(16:0/18:0), also known as pSer(34:0), 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(16:0/18:0) is considered to be a glycerophosphoserine lipid molecule. PS(16:0/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(16:0/18:0) exists in all eukaryotes, ranging from yeast to humans. PS(16:0/18:0) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(16:0/18:0) can be biosynthesized from PC(16:0/18:0) and L-serine through the action of the enzyme phosphatidylserine synthase. In addition, PS(16:0/18:0) can be converted into PE(16:0/18:0); which is catalyzed by the enzyme phosphatidylserine decarboxylase. In cattle, PS(16:0/18:0) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(16:0/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoserineChEBI
Phosphatidylserine(16:0/18:0)ChEBI
pSer(16:0/18:0)ChEBI
pSer(34:0)ChEBI
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(34:0)HMDB
PS(34:0)HMDB
PS(16:0/18:0)Lipid Annotator
Chemical FormulaC40H78NO10P
Average Molecular Weight764.035
Monoisotopic Molecular Weight763.536334714
IUPAC Name(2S)-2-amino-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)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)CCCCCCCCCCCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C40H78NO10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(43)51-36(34-49-52(46,47)50-35-37(41)40(44)45)33-48-38(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h36-37H,3-35,41H2,1-2H3,(H,44,45)(H,46,47)/t36-,37+/m1/s1
InChI KeyUYGORIHCWHGAJE-AARKOHAPSA-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
logP4.66ALOGPS
logP10.38ChemAxon
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 Count42ChemAxon
Refractivity206.04 m³·mol⁻¹ChemAxon
Polarizability92.59 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-9050110300-c262247243572bc1bb9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9030000000-5116012bb815f612914cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9161011000-da017f416cf9577f9e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bwi-1190101200-0dd08757f03ce0fe37edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7r-4290100000-d4d72bb13b64cc9a48d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030100000-db0d1b7861f28b1c00c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-6d0e0b3ff89333a0d01fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000001900-7de223fdab2105ef80a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07gl-0194606400-cda9cf95fecbf3a2f33eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ji-0000099900-5662b22b0af52dbd4e05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00jo-0900099900-83d204d3e0a9d5d6ba52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00jo-0900099900-83d204d3e0a9d5d6ba52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0000016900-6b4025fdec4204eaaa44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000002900-ea8f127ba2255b6e1233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090014100-d36aa2bc676f7bfcacd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-41f2a0e39076295cb53cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0002291400-ab039215d97ace341416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0002291100-0460e9e3bac6fbb1c4f7View 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 IDHMDB0012356
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028974
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926014
PDB IDNot Available
ChEBI ID84520
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(16:0/18:0) → PE(16:0/18:0) + 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(16:0/18:0) + L-Serine → Choline + PS(16:0/18:0)details