Showing metabocard for PS(16:1(9Z)/18:1(9Z)) (BMDB0012368)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:02 UTC
Update Date2020-05-21 16:28:18 UTC
BMDB IDBMDB0012368
Secondary Accession Numbers
  • BMDB12368
Metabolite Identification
Common NamePS(16:1(9Z)/18:1(9Z))
DescriptionPS(16:1(9Z)/18:1(9Z)), also known as ps(16:1(9z)/18:1(9z)) or PS(16:1/18:1), 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(16:1(9Z)/18:1(9Z)) is considered to be a glycerophosphoserine lipid molecule. PS(16:1(9Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PS(16:1(9Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PS(16:1(9Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(16:1(9Z)/18:1(9Z)) can be biosynthesized from PC(16:1(9Z)/18:1(9Z)) and L-serine; which is mediated by the enzyme phosphatidylserine synthase. Furthermore, PS(16:1(9Z)/18:1(9Z)) can be converted into PE(16:1(9Z)/18:1(9Z)) through the action of the enzyme phosphatidylserine decarboxylase. Finally, PS(16:1(9Z)/18:1(9Z)) can be converted into PE(16:1(9Z)/18:1(9Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PS(16:1(9Z)/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:1(9Z)) pathway and phosphatidylcholine biosynthesis PC(16:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(16:1/18:1)HMDB
Phosphatidylserine(16:1n7/18:1n9)HMDB
Phosphatidylserine(16:1W7/18:1W9)HMDB
Phosphatidylserine(34:2)HMDB
PS(16:1/18:1)HMDB
PS(16:1N7/18:1N9)HMDB
PS(16:1W7/18:1W9)HMDB
PS(34:2)HMDB
pSer(16:1/18:1)HMDB
pSer(16:1n7/18:1n9)HMDB
pSer(16:1W7/18:1W9)HMDB
pSer(34:2)HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoserineHMDB
PS(16:1(9Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC40H74NO10P
Average Molecular Weight760.003
Monoisotopic Molecular Weight759.505034585
IUPAC Name(2S)-2-amino-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C40H74NO10P/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/h14,16-18,36-37H,3-13,15,19-35,41H2,1-2H3,(H,44,45)(H,46,47)/b16-14-,18-17-/t36-,37+/m1/s1
InChI KeyISTSBKDAWNZURU-KQQJSZDRSA-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
logP4.62ALOGPS
logP9.66ChemAxon
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 Count40ChemAxon
Refractivity208.27 m³·mol⁻¹ChemAxon
Polarizability89.23 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-9050110400-fe3b4c558ff1191e79e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9030000000-adaeba895a458c198a60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9161011000-95266e90c45c52202316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zgr-1190101200-6d38edeae3dd6fc63184View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugr-4290100000-ee8f58397d99a1d0cd74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030100000-66cea49eeefe9e05fc89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0000099900-65dfe0284c3432521e46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ou-0900099900-d09ba80dc2f5e7e887faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-0900099900-d09ba80dc2f5e7e887faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0000016900-de056cdff70a6b313bb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000002900-41f64a2dc17b794381fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090033100-30ac58a03625879aca0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000010900-07c6b63d9f9a1fb7829bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0002291400-9b5aa0de989a263b78f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0002291100-5e84ac342423ee041048View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000900-6243644009b9d2eab214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000001900-f30b3a04dcd32c4f4035View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0l7r-0194606400-8c042d8dd6269fd5f11aView 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 IDHMDB0012368
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028986
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926009
PDB IDNot Available
ChEBI ID90032
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(16:1(9Z)/18:1(9Z)) → PE(16:1(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(16:1(9Z)/18:1(9Z)) + L-Serine → Choline + PS(16:1(9Z)/18:1(9Z))details