Showing metabocard for PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) (BMDB0010166)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:01:10 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0010166
Secondary Accession Numbers
  • BMDB10166
Metabolite Identification
Common NamePS(18:0/22:5(7Z,10Z,13Z,16Z,19Z))
DescriptionPS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)), also known as ps(18:0/22:5(7z,10z,13z,16z,19z)) or PS(18:0/22:5), 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. PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) is possibly soluble (in water) and a very strong basic compound (based on its pKa). PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, Choline and PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) and L-serine through its interaction with the enzyme phosphatidylserine synthase. Furthermore, PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) through the action of the enzyme phosphatidylserine decarboxylase. Finally, PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) can be converted into PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidylserine decarboxylase. In cattle, PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylethanolamine biosynthesis pe(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylcholine biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Stearoyl-2-docosapentaenoyl-sn-glycero-3-phosphoserineHMDB
Phosphatidylserine(18:0/22:5)HMDB
Phosphatidylserine(18:0/22:5n3)HMDB
Phosphatidylserine(18:0/22:5W3)HMDB
Phosphatidylserine(40:5)HMDB
PS(18:0/22:5)HMDB
PS(18:0/22:5N3)HMDB
PS(18:0/22:5W3)HMDB
PS(40:5)HMDB
pSer(18:0/22:5)HMDB
pSer(18:0/22:5n3)HMDB
pSer(18:0/22:5W3)HMDB
pSer(40:5)HMDB
1-Octadecanoyl-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphoserineHMDB
PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC46H80NO10P
Average Molecular Weight838.1019
Monoisotopic Molecular Weight837.551984297
IUPAC Name(2S)-2-amino-3-({[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O
InChI Identifier
InChI=1S/C46H80NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-45(49)57-42(40-55-58(52,53)56-41-43(47)46(50)51)39-54-44(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,42-43H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,28-26-/t42-,43+/m1/s1
InChI KeyPZEFRSYCROBXSJ-AOWFZNJASA-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 DescriptorsNot Available
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
logP5.32ALOGPS
logP11.24ChemAxon
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 Count43ChemAxon
Refractivity239.22 m³·mol⁻¹ChemAxon
Polarizability97.15 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, Positivesplash10-000l-9022010120-e0072c6e835435ed7711View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9011000100-909caede3cd70b0c084fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9054002000-f783ca8ecf29e5d3a237View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-017i-2193030230-4f3553eb8bfa89ae7dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5291010000-2c45209cee9da5710cc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9021000000-206a313c08c5f03e948cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000001090-c68a6ab535aad8a24006View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0003069160-9f98b1951499209a5647View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0003069110-f03c5e61259fcbfdf236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-eecf3b610497c882b440View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000000190-852cd9d61d99074fe56fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017s-0033900530-3ba7e2df70decd56560bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-14i6-0000009990-c5a505ddd62ffb8ca3dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0900009990-8c00ecfa4b8a3fcfa26bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-0900009990-8c00ecfa4b8a3fcfa26bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0000001690-65d943e1c96c2c697b61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000290-9cad889415ece7583a31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090003310-2a935c4707fc9400ebe6View 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 IDHMDB0010166
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027349
KNApSAcK IDNot Available
Chemspider ID24768057
KEGG Compound IDC02737
BioCyc IDL-1-PHOSPHATIDYL-SERINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480355
PDB IDNot Available
ChEBI ID90040
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(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) → PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) + 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(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z))details