Showing metabocard for PS(18:0/18:0) (BMDB0012378)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:14 UTC
Update Date2020-05-21 16:28:19 UTC
BMDB IDBMDB0012378
Secondary Accession Numbers
  • BMDB12378
Metabolite Identification
Common NamePS(18:0/18:0)
DescriptionPS(18:0/18:0), also known as pSer(36:0), 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(18:0/18:0) is considered to be a glycerophosphoserine lipid molecule. PS(18:0/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:0/18:0) exists in all eukaryotes, ranging from yeast to humans. PS(18:0/18:0) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:0/18:0) can be biosynthesized from PC(18:0/18:0) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. In addition, PS(18:0/18:0) can be converted into PE(18:0/18:0); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:0/18:0) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(18:0/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dioctadecanoyl-sn-glycero-3-phosphoserineChEBI
Distearoyl phosphatidylserineChEBI
Phosphatidylserine(18:0/18:0)ChEBI
Phosphatidylserine(36:0)ChEBI
pSer(18:0/18:0)ChEBI
pSer(36:0)ChEBI
1,2-Distearoyl-rac-glycero-3-phosphoserineHMDB
PS(36:0)HMDB
1,2-Dioctadecanoyl-rac-glycero-3-phosphoserineHMDB
PS(18:0/18:0)Lipid Annotator
Chemical FormulaC42H82NO10P
Average Molecular Weight792.089
Monoisotopic Molecular Weight791.567634842
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Namedistearoyl phosphatidylserine
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C42H82NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h38-39H,3-37,43H2,1-2H3,(H,46,47)(H,48,49)/t38-,39+/m1/s1
InChI KeyTZCPCKNHXULUIY-RGULYWFUSA-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
logP4.95ALOGPS
logP11.27ChemAxon
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 Count44ChemAxon
Refractivity215.24 m³·mol⁻¹ChemAxon
Polarizability96.15 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
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-00di-0000000900-22591428bb6273131cdcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-00di-0010000900-ba4725252c743910fc6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 49V, negativesplash10-00di-0030000900-cf3c4f9f64b537902839View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-0089-0090000600-48210c75c026547a63afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-001i-0090000100-ec3346405e185878d998View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 82V, negativesplash10-001i-0090000000-89495dcfc466d296908eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 98V, negativesplash10-001i-0090000000-4568190f9e65c021c183View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 120V, negativesplash10-001i-1190000000-3fa25288c531b8c8546bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 142V, negativesplash10-003r-4290000000-ce23c4801ecc40c857d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 175V, negativesplash10-004i-9110000000-81aea2b780940befed87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-001i-0090210000-9f1730651a0fbc8977bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-001i-0090000000-1dfdc3824df469b8ca7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-001i-0090000000-9c09632abef0d1b601bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004j-9000000000-4db762aff12b7cd28a70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-001i-0090000000-6da632a0f6c80497dbf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0006-0000000900-ad43347e0c2b9f181d11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 49V, negativesplash10-0f6x-0000200900-955d6c499624cfead776View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, negativesplash10-0gb9-0020900300-6912159483890a11c7f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 80V, negativesplash10-001i-1290300000-491b8e236ede430a15e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020120400-fcdc30f10d82fdda5f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010000000-798fe1f94003146dddccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9033012100-5441754e2cc7cc4f3a80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00si-1190130500-5b1e74195d04be9bdfc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110100-565b2aaae023469aafb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-a4c21235308cfbf9bd0bView 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 IDHMDB0012378
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028996
KNApSAcK IDNot Available
Chemspider ID7826046
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547096
PDB IDP5S
ChEBI ID84519
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(18:0/18:0) → PE(18:0/18:0) + 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(18:0/18:0) + L-Serine → Choline + PS(18:0/18:0)details