Showing metabocard for PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (BMDB0012444)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:39 UTC
Update Date2020-05-11 20:27:10 UTC
BMDB IDBMDB0012444
Secondary Accession Numbers
  • BMDB12444
Metabolite Identification
Common NamePS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)
DescriptionPS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0), in particular, consists of one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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-Docosahexaenoyl-2-stearoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(22:6/18:0)HMDB
Phosphatidylserine(22:6n3/18:0)HMDB
Phosphatidylserine(22:6W3/18:0)HMDB
Phosphatidylserine(40:6)HMDB
PS(22:6/18:0)HMDB
PS(22:6N3/18:0)HMDB
PS(22:6W3/18:0)HMDB
PS(40:6)HMDB
pSer(22:6/18:0)HMDB
pSer(22:6n3/18:0)HMDB
pSer(22:6W3/18:0)HMDB
pSer(40:6)HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-octadecanoyl-sn-glycero-3-phosphoserineHMDB
PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)Lipid Annotator
Chemical FormulaC46H78NO10P
Average Molecular Weight836.086
Monoisotopic Molecular Weight835.536334233
IUPAC Name(2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C46H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,18,20,23-24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,27-25-,33-31-/t42-,43+/m1/s1
InChI KeyYZPDRIODLGOXPQ-VQXQEPRVSA-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
logP5.28ALOGPS
logP10.88ChemAxon
logS-7.1ALOGPS
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
Refractivity240.34 m³·mol⁻¹ChemAxon
Polarizability96.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ku-9021010120-5e578bffbe9affc1ad24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9020000100-66bc1af211dbed25eef6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9054002000-f790d54bb34a9b7b0331View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05q9-2149030230-9aa4e7aa2ab9181f2113View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-6339110100-ebc1c9ac533e2ba39614View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9111000000-ef9c0a8e4dc570c93ca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000001690-20dcfbf541932cce0814View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000290-02e5e14a99d9dff509bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-5e5d56c271157aa256d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001090-faf723827f4ade208e21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0003069160-2bb5ae2dbcd293b7c496View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0003069110-08b2824deac14ebb4703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000009990-8e93140100e6176c905cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0900009990-a5b17ec774a9b41c38f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0900009990-a5b17ec774a9b41c38f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-6191c307c20fd8a43f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000190-3b47bde727731c95bd2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-0033900530-5f552651f33c4f460fbdView 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 IDHMDB0012444
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029060
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52925937
PDB IDNot Available
ChEBI ID88445
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available