Showing metabocard for PS(18:1(9Z)/18:0) (BMDB0012389)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:37:26 UTC
Update Date2020-05-11 20:26:25 UTC
BMDB IDBMDB0012389
Secondary Accession Numbers
  • BMDB12389
Metabolite Identification
Common NamePS(18:1(9Z)/18:0)
DescriptionPS(18:1(9Z)/18:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. 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 atoms. PS(18:1(9Z)/18:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one octadecanoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z)-Octadecenoyl-2-octadecanoyl-sn-glycero-3-phospho-L-serineChEBI
1-(9Z-Octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphoserineChEBI
1-C18:1(Omega-9)-2-C18:0-phosphatidylserineChEBI
1-Oleoyl-2-stearoyl-sn-glycero-3-phosphoserineChEBI
O-{hydroxy[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(stearoyloxy)propoxy]phosphoryl}-L-serineChEBI
Phosphatidylserine(18:1/18:0)ChEBI
Phosphatidylserine(18:1omega9/18:0)ChEBI
Phosphatidylserine(36:1)ChEBI
PS(18:1/18:0)ChEBI
PS(18:1OMEGA9/18:0)ChEBI
PS(36:1)ChEBI
Phosphatidylserine(18:1n9/18:0)HMDB
Phosphatidylserine(18:1W9/18:0)HMDB
PS(18:1N9/18:0)HMDB
PS(18:1W9/18:0)HMDB
pSer(18:1/18:0)HMDB
pSer(18:1n9/18:0)HMDB
pSer(18:1W9/18:0)HMDB
pSer(36:1)HMDB
PS(18:1(9Z)/18:0)Lipid Annotator
Chemical FormulaC42H80NO10P
Average Molecular Weight790.073
Monoisotopic Molecular Weight789.551984778
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy((2R)-3-[(9Z)-octadec-9-enoyloxy]-2-(octadecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O
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/h17,19,38-39H,3-16,18,20-37,43H2,1-2H3,(H,46,47)(H,48,49)/b19-17-/t38-,39+/m1/s1
InChI KeyVYDABBXFPODZIE-IAJQVIMPSA-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
Polarizability95.07 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ku-9040110400-e668c1a2a6e5a5e70945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9020000000-fb653ad9d007447436e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9043001100-74b7619e40bcaa0f102bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-1190030400-54ad37574c3c1c3bdc41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390110100-2170c31910998c8cb4b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9120100000-34171ff0512d64687fb4View 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, 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, 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
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 IDHMDB0012389
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029005
KNApSAcK IDNot Available
Chemspider ID7826044
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547094
PDB IDNot Available
ChEBI ID75103
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available