Showing metabocard for PS(18:0/18:3(9Z,12Z,15Z)) (BMDB0012381)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:17 UTC
Update Date2020-05-21 16:28:19 UTC
BMDB IDBMDB0012381
Secondary Accession Numbers
  • BMDB12381
Metabolite Identification
Common NamePS(18:0/18:3(9Z,12Z,15Z))
DescriptionPS(18:0/18:3(9Z,12Z,15Z)), also known as ps(18:0/18:3(9z,12z,15z)) or PS(18:0/18:3), 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(18:0/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:0/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:0/18:3(9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:0/18:3(9Z,12Z,15Z)) can be biosynthesized from PC(18:0/18:3(9Z,12Z,15Z)) and L-serine through the action of the enzyme phosphatidylserine synthase. Furthermore, PS(18:0/18:3(9Z,12Z,15Z)) can be converted into PE(18:0/18:3(9Z,12Z,15Z)) through the action of the enzyme phosphatidylserine decarboxylase. Finally, PS(18:0/18:3(9Z,12Z,15Z)) can be converted into PE(18:0/18:3(9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:0/18:3(9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:0/18:3(9Z,12Z,15Z)) pathway and phosphatidylcholine biosynthesis PC(18:0/18:3(9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearoyl-2-a-linolenoyl-sn-glycero-3-phosphoserineHMDB
1-Stearoyl-2-alpha-linolenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:0/18:3)HMDB
Phosphatidylserine(18:0/18:3n3)HMDB
Phosphatidylserine(18:0/18:3W3)HMDB
Phosphatidylserine(36:3)HMDB
PS(18:0/18:3)HMDB
PS(18:0/18:3N3)HMDB
PS(18:0/18:3W3)HMDB
PS(36:3)HMDB
pSer(18:0/18:3)HMDB
pSer(18:0/18:3n3)HMDB
pSer(18:0/18:3W3)HMDB
pSer(36:3)HMDB
1-Octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:0/18:3(9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC42H76NO10P
Average Molecular Weight786.0273
Monoisotopic Molecular Weight785.520684169
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)C(O)=O
InChI Identifier
InChI=1S/C42H76NO10P/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/h6,8,12,14,18,20,38-39H,3-5,7,9-11,13,15-17,19,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b8-6-,14-12-,20-18-/t38-,39+/m1/s1
InChI KeyFJJVJFAWOZTCBP-XCOFVSEPSA-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
logP4.93ALOGPS
logP10.19ChemAxon
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 Count41ChemAxon
Refractivity218.59 m³·mol⁻¹ChemAxon
Polarizability92.04 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, Positivesplash10-000l-9030020400-187af68c3c39008bea62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9020000000-ef8dc47af964b9da7621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9043010000-f55b551468de4ffc2107View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-2190031300-6d190230fde434e3c4faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5290010000-95aafab9b19a00d548feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120000000-a609be4061dae187cad3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000001690-bb2913e7a32cc26ef2b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000290-92f757f0b9b9f8d7a9d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-f294bda926ae3d46c9fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001900-350a0a60ae8b9c7a1402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0002059500-fefc769b5a3f6cef0dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0002059100-172c5e72a5629c18b04cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000004900-b6e4d4ac0adcb6ea37e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0400004900-884a5b50daedd22b8baeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0400004900-884a5b50daedd22b8baeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-842b0ebd6ec927ad317bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000001900-a07ecdca833dcd2aa01aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0070905300-4cea400410242bb56bf1View 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 IDHMDB0012381
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028998
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925426
PDB IDNot Available
ChEBI ID90017
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(18:0/18:3(9Z,12Z,15Z)) → PE(18:0/18:3(9Z,12Z,15Z)) + 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(18:0/18:3(9Z,12Z,15Z)) + L-Serine → Choline + PS(18:0/18:3(9Z,12Z,15Z))details