Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 20:01:17 UTC
Update Date2022-11-30 19:24:43 UTC
HMDB IDHMDB0112830
Secondary Accession NumbersNone
Metabolite Identification
Common NamePS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z))
DescriptionPS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 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 positions. PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of osbond acid at the C-1 position and one chain of eicosatetraenoic acid at the C-2 position. 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 group). As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate 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 a 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
Data?1563873298
Synonyms
ValueSource
1-osbondoyl-2-eicosatetraenoyl-sn-glycero-3-phosphoserine SMPDB, HMDB
PS(22:5/20:4) SMPDB, HMDB
PS(22:5n6/20:4n3) SMPDB, HMDB
PS(22:5w6/20:4w3) SMPDB, HMDB
PS(42:9) SMPDB, HMDB
Pser(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) SMPDB, HMDB
Pser(22:5/20:4) SMPDB, HMDB
Pser(22:5n6/20:4n3) SMPDB, HMDB
Pser(22:5w6/20:4w3) SMPDB, HMDB
Pser(42:9) SMPDB, HMDB
Phosphatidylserine(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) SMPDB, HMDB
Phosphatidylserine(22:5/20:4) SMPDB, HMDB
Phosphatidylserine(22:5n6/20:4n3) SMPDB, HMDB
Phosphatidylserine(22:5w6/20:4w3) SMPDB, HMDB
Phosphatidylserine(42:9)SMPDB, HMDB
PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z))SMPDB
PSer(42:9)Lipid Annotator
PS(42:9)Lipid Annotator
1-osbondoyl-2-eicsoatetraenoyl-sn-glycero-3-phosphoserineLipid Annotator, HMDB
PSer(22:5/20:4)Lipid Annotator
PS(22:5/20:4)Lipid Annotator
Phosphatidylserine(22:5/20:4)Lipid Annotator
1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphoserineLipid Annotator, HMDB
(2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoateGenerator, HMDB
Chemical FormulaC48H76NO10P
Average Molecular Weight858.107
Monoisotopic Molecular Weight857.520684649
IUPAC Name(2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]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/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O
InChI Identifier
InChI=1S/C48H76NO10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-46(50)56-41-44(42-57-60(54,55)58-43-45(49)48(52)53)59-47(51)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,22,24,26-29,33,35,44-45H,3-5,7,9-10,15-16,21,23,25,30-32,34,36-43,49H2,1-2H3,(H,52,53)(H,54,55)/b8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,35-33-/t44-,45+/m1/s1
InChI KeyGTXANKIFLLUONJ-OAMNLSDQSA-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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.1ALOGPS
logP10.68ChemAxon
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 Count41ChemAxon
Refractivity252.89 m³·mol⁻¹ChemAxon
Polarizability96.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+292.25430932474
DeepCCS[M-H]-289.87730932474
DeepCCS[M-2H]-323.6530932474
DeepCCS[M+Na]+298.28430932474
AllCCS[M+H]+298.532859911
AllCCS[M+H-H2O]+298.532859911
AllCCS[M+NH4]+298.532859911
AllCCS[M+Na]+298.532859911
AllCCS[M-H]-300.732859911
AllCCS[M+Na-2H]-308.032859911
AllCCS[M+HCOO]-316.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z))[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/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O6449.7Standard polar33892256
PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z))[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/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O5257.4Standard non polar33892256
PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z))[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/CCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)C(O)=O6097.8Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Positive-QTOFsplash10-001l-0000001690-c36f1bff88e8a5d985b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Positive-QTOFsplash10-001i-0000000290-b9e7c58f4d17130e834f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Positive-QTOFsplash10-0a4i-0090003310-ce9c028043cb48f10f512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Negative-QTOFsplash10-0a4i-0000000090-0a9c43ee86c55930e2812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Negative-QTOFsplash10-0a4i-0000000190-b59dbe029fe0f0ddfc8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Negative-QTOFsplash10-0ldi-0007900530-4757a2bfd3968c08d6d42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Positive-QTOFsplash10-0a4i-0000001090-eea8f8930a9d5c7bea832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Positive-QTOFsplash10-05fr-0003069160-ce772c86dc3adaf120632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Positive-QTOFsplash10-00di-0003069110-f919b385b3cfdcf958862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Positive-QTOFsplash10-03vi-0000009990-2b184d2d98081c3ef99c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Positive-QTOFsplash10-03vo-0900009990-bd861168a98576d0903c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Positive-QTOFsplash10-03vo-0900009990-bd861168a98576d0903c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131819961
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available