Showing metabocard for PS(18:1(9Z)/18:1(9Z)) (BMDB0012390)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:27 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0012390
Secondary Accession Numbers
  • BMDB12390
Metabolite Identification
Common NamePS(18:1(9Z)/18:1(9Z))
DescriptionPS(18:1(9Z)/18:1(9Z)), also known as ps(18:1(9z)/18:1(9z))e or 1,2-DLPS, 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(18:1(9Z)/18:1(9Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:1(9Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:1(9Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PS(18:1(9Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:1(9Z)/18:1(9Z)) can be biosynthesized from PC(18:1(9Z)/18:1(9Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. In addition, PS(18:1(9Z)/18:1(9Z)) can be converted into PE(18:1(9Z)/18:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:1(9Z)/18:1(9Z)) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dioleoyl-sn-glycero-3-phosphoserineChEBI
1,2-DioleoylphosphatidylserineChEBI
1,2-DLPSChEBI
Dioleoyl phosphatidylserineChEBI
DOPSChEBI
DOPSEChEBI
Phosphatidylserine(18:1/18:1)ChEBI
Phosphatidylserine(18:1omega9/18:1omega9)ChEBI
Phosphatidylserine(36:2)ChEBI
PS(18:1/18:1)ChEBI
PS(18:1OMEGA9/18:1OMEGA9)ChEBI
PS(36:2)ChEBI
1,2-Dioleoyl-rac-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:1n9/18:1n9)HMDB
Phosphatidylserine(18:1W9/18:1W9)HMDB
PS(18:1N9/18:1N9)HMDB
PS(18:1W9/18:1W9)HMDB
pSer(18:1/18:1)HMDB
pSer(18:1n9/18:1n9)HMDB
pSer(18:1W9/18:1W9)HMDB
pSer(36:2)HMDB
1,2-Dioleoylphosphatidylserine, monosodium salt, (R-(Z,Z))-isomerHMDB
1,2-Dioleoylphosphatidylserine, sodium salt, (Z,Z)-isomerHMDB
1,2-Dioleoylphosphatidylserine, (Z,Z)-isomerHMDB
1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phosphoserineHMDB
PS(18:1(9Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC42H78NO10P
Average Molecular Weight788.057
Monoisotopic Molecular Weight787.536334714
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional NameDOPS
CAS Registry Number70614-14-1
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C42H78NO10P/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/h17-20,38-39H,3-16,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b19-17-,20-18-/t38-,39+/m1/s1
InChI KeyWTBFLCSPLLEDEM-JIDRGYQWSA-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
logP4.96ALOGPS
logP10.55ChemAxon
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
Refractivity217.47 m³·mol⁻¹ChemAxon
Polarizability93.32 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 - IT 40V, negativesplash10-015a-0130905000-d8f46442e4e3c7adefb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-014i-0000000900-cf40d0ddb17ab7974b2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-014i-0010000900-aadf954c64f212ee11f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-016r-0040000900-d7953ea3372a35e684abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-00or-0090000700-0715d812928b42a7715bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-004i-0090000100-ce0d176424e9c1a4f9fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 80V, negativesplash10-004i-0090000000-f158e209a254a9ce3737View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 97V, negativesplash10-004i-0090000000-71551f9569be509f99aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 119V, negativesplash10-004i-1190000000-9ed3d13d5b84f65074cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 141V, negativesplash10-004i-7390000000-9f14978138420782a4feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 173V, negativesplash10-004i-9100000000-da1c2f0fd31c179420bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090210000-757499483c20b79dd5d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090000000-cd763c6dcf40c4ec2356View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-06r6-1190000000-ba930116c1335ab330bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004i-0090000000-52430f6dfd091c56b260View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-004j-9000000000-44c080f0b731402e500cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-000i-0000000900-1c12b250e6fed3ac7e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000j-0000407900-9030c795256b7df30091View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, negativesplash10-014i-1030903000-e20c6f02695a38934804View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020120400-98e01c33f1aa8610b08dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9010000000-f9f138a277fa485d97c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9023011100-8497477243b05d931f5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-1190132300-8af751ae39bd84c631a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110000-38da08ecdf851290d577View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-cf3378ec40f70542a26dView 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 IDHMDB0012390
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029006
KNApSAcK IDNot Available
Chemspider ID4943103
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438639
PDB ID17F
ChEBI ID60568
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(18:1(9Z)/18:1(9Z)) → PE(18:1(9Z)/18:1(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(18:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(18:1(9Z)/18:1(9Z))details