Showing metabocard for PS(18:0/18:1(9Z)) (BMDB0010163)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:01:06 UTC
Update Date2020-05-21 16:28:19 UTC
BMDB IDBMDB0010163
Secondary Accession Numbers
  • BMDB10163
Metabolite Identification
Common NamePS(18:0/18:1(9Z))
DescriptionPS(18:0/18:1(9Z)), also known as 18:0-18:1-PS or PS(18:0/18:1), 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(18:0/18:1(9Z)) is considered to be a glycerophosphoserine lipid molecule. PS(18:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(18:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PS(18:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:0/18:1(9Z)) can be biosynthesized from PC(18:0/18:1(9Z)) and L-serine; which is catalyzed by the enzyme phosphatidylserine synthase. In addition, PS(18:0/18:1(9Z)) can be converted into PE(18:0/18:1(9Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:0/18:1(9Z)) is involved in the metabolic pathway called phosphatidylethanolamine biosynthesis pe(18:0/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-18:0-2-18:1-PhosphatidylserineChEBI
1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoserineChEBI
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoserineChEBI
18:0-18:1-PSChEBI
O-{hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(stearoyloxy)propoxy]phosphoryl}-L-serineChEBI
Phosphatidyl-L-serine (1-18:0-2-18:1)ChEBI
Phosphatidylserine(18:0/18:1)ChEBI
Phosphatidylserine(18:0/18:1n9)ChEBI
Phosphatidylserine(18:0/18:1W9)ChEBI
Phosphatidylserine(36:1)ChEBI
PS(18:0/18:1)ChEBI
PS(18:0/18:1N9)ChEBI
PS(18:0/18:1W9)ChEBI
PS(36:1)ChEBI
pSer(18:0/18:1)ChEBI
pSer(18:0/18:1n9)ChEBI
pSer(18:0/18:1W9)ChEBI
pSer(36:1)ChEBI
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphoserineHMDB
1-Stearoyl-2-oleoyl-GPSHMDB
Phosphatidylserine(18:0/18:1(9Z))HMDB
pSer(18:0/18:1(9Z))HMDB
PS(18:0/18:1(9Z))Lipid Annotator
Chemical FormulaC42H80NO10P
Average Molecular Weight790.073
Monoisotopic Molecular Weight789.551984778
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H80NO10P/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/h18,20,38-39H,3-17,19,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b20-18-/t38-,39+/m1/s1
InChI KeyAJFWREUFUPEYII-PAHWMLEVSA-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
logP10.91ChemAxon
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 Count43ChemAxon
Refractivity216.35 m³·mol⁻¹ChemAxon
Polarizability94.89 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9020120400-8b3abf5ee490081655e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9010000000-6b12a96913918691d068View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9033011100-c3cb36db3c464cb00b34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1190030400-c27322c37aa82f6bfec3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110100-2b169a92a9dd7bbe9b3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-004f297a75be7d9fe009View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000001900-92358d2708fbe52da6aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0003069700-0b11fc1d31df804fe9bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0003069300-1f2b15ffbc23b6d8895cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0000004900-8ddd472a449c7238e6d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4m-0400004900-d50ddf3988d0dcf20378View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-0400004900-d50ddf3988d0dcf20378View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-fe622cdc999efc524fd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000900-a50108dabb7bd3623c4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gd0-0070900800-281b84595f9bb7100373View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0000001690-dab1e81094b582889f19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000290-ec13b6db523d0d9d58ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-37d350319f45448a6c64View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
  • Heart
  • Kidney
  • Liver
  • Placenta
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
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010163
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027346
KNApSAcK IDNot Available
Chemspider ID7826037
KEGG Compound IDC02737
BioCyc IDCPD-8336
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound59720717
PDB IDNot Available
ChEBI ID79096
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(18:0/18:1(9Z)) → PE(18:0/18:1(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(18:0/18:1(9Z)) + L-Serine → Choline + PS(18:0/18:1(9Z))details