Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:58:53 UTC
Update Date2022-11-30 19:24:26 UTC
HMDB IDHMDB0112269
Secondary Accession NumbersNone
Metabolite Identification
Common NamePS(18:1(11Z)/14:0)
DescriptionPS(18:1(11Z)/14:0) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:1(11Z)/14:0), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of myristic acid at the C-2 position. 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. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. Phosphatidylserines typically carry a net charge of -1 at physiological pH. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
Structure
Data?1563873236
Synonyms
ValueSource
PS(18:1/14:0)Lipid Annotator, HMDB
Phosphatidylserine(18:1/14:0)Lipid Annotator, HMDB
PS(32:1)Lipid Annotator, HMDB
PS(18:1(11Z)/14:0)Lipid Annotator
PSer(18:1/14:0)Lipid Annotator, HMDB
PSer(32:1)Lipid Annotator, HMDB
1-vaccenoyl-2-myristoyl-sn-glycero-3-phosphoserineLipid Annotator, HMDB
1-(11Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphoserineLipid Annotator, HMDB
Phosphatidylserine(32:1)Lipid Annotator, HMDB
Chemical FormulaC38H72NO10P
Average Molecular Weight733.965
Monoisotopic Molecular Weight733.48938452
IUPAC Name(2S)-2-amino-3-({hydroxy[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[hydroxy((2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C38H72NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-19-14-12-10-8-6-4-2/h13,15,34-35H,3-12,14,16-33,39H2,1-2H3,(H,42,43)(H,44,45)/b15-13-/t34-,35+/m1/s1
InChI KeyNEAKGADOSSEPBF-NUZFNMCPSA-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.
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
  • Fatty acyl
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxygen compound
  • Amine
  • 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
logP4.29ALOGPS
logP9.13ChemAxon
logS-6.8ALOGPS
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 Count39ChemAxon
Refractivity197.95 m³·mol⁻¹ChemAxon
Polarizability86.43 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
DarkChem[M+H]+280.01431661259
DarkChem[M-H]-268.9331661259
DeepCCS[M+H]+277.88730932474
DeepCCS[M-H]-275.82230932474
DeepCCS[M-2H]-309.06430932474
DeepCCS[M+Na]+283.830932474
AllCCS[M+H]+280.032859911
AllCCS[M+H-H2O]+279.832859911
AllCCS[M+NH4]+280.132859911
AllCCS[M+Na]+280.132859911
AllCCS[M-H]-270.832859911
AllCCS[M+Na-2H]-276.432859911
AllCCS[M+HCOO]-282.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PS(18:1(11Z)/14:0)[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O4937.5Standard polar33892256
PS(18:1(11Z)/14:0)[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O4554.4Standard non polar33892256
PS(18:1(11Z)/14:0)[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=O5195.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PS(18:1(11Z)/14:0),2TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC5017.3Semi standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC4350.8Standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC7021.1Standard polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #2CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC5095.4Semi standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #2CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC4585.7Standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #2CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC6626.8Standard polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #3CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC5145.2Semi standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #3CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC4583.2Standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #3CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC6107.9Standard polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #4CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC5321.7Semi standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #4CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC4660.9Standard non polar33892256
PS(18:1(11Z)/14:0),2TMS,isomer #4CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC6719.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PS(18:1(11Z)/14:0) GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 10V, Positive-QTOFsplash10-0udq-0000099900-16b00907a872a97f604d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 20V, Positive-QTOFsplash10-0f6y-0900099900-27f7885dd92a75f026072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 40V, Positive-QTOFsplash10-0f6y-0900099900-27f7885dd92a75f026072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 10V, Positive-QTOFsplash10-001i-0000010900-a3618ed5c0977a9c16662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 20V, Positive-QTOFsplash10-000t-0011291400-fc10496fffa5e15365f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 40V, Positive-QTOFsplash10-0002-0011291100-915123c6f35906a54f6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 10V, Negative-QTOFsplash10-001i-0000000900-9a9bb283980a30a345962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 20V, Negative-QTOFsplash10-001i-0000001900-9985a2da99ac0cb010602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 40V, Negative-QTOFsplash10-001j-0195506400-6a7d02998e08fe34cd7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 10V, Positive-QTOFsplash10-0aor-0000016900-b107e77e52b30f34c7682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 20V, Positive-QTOFsplash10-0a4i-0000002900-a46a689e8afcd394281b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PS(18:1(11Z)/14:0) 40V, Positive-QTOFsplash10-0a4i-0090033100-f7645ecb61a95f9336da2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart 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 Compound131819693
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP: Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998 Jan 1;31(1):1-9. [PubMed:9450519 ]
  7. Vance JE, Tasseva G: Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim Biophys Acta. 2013 Mar;1831(3):543-54. doi: 10.1016/j.bbalip.2012.08.016. Epub 2012 Aug 29. [PubMed:22960354 ]
  8. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  10. Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..