Showing Compound Card for PS(22:1(13Z)/22:1(13Z)) (CDB003286)

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Record Information
Version1.0
Created at2020-03-30 20:34:19 UTC
Updated at2020-11-18 16:38:16 UTC
CannabisDB IDCDB003286
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePS(22:1(13Z)/22:1(13Z))
DescriptionPS(22:1(13Z)/22:1(13Z)) 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(22:1(13Z)/22:1(13Z)), in particular, consists of two 13Z-docosenoyl chains at positions C-1 and C-2. 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. This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Erucoyl-2-erucoyl-sn-glycero-3-phosphoserineHMDB
PS(22:1/22:1)HMDB
PS(22:1N9/22:1N9)HMDB
PS(22:1W9/22:1W9)HMDB
PS(44:2)HMDB
pSer(22:1(13Z)/22:1(13Z))HMDB
pSer(22:1/22:1)HMDB
pSer(22:1n9/22:1n9)HMDB
pSer(22:1W9/22:1W9)HMDB
pSer(44:2)HMDB
Phosphatidylserine(22:1(13Z)/22:1(13Z))HMDB
Phosphatidylserine(22:1/22:1)HMDB
Phosphatidylserine(22:1n9/22:1n9)HMDB
Phosphatidylserine(22:1W9/22:1W9)HMDB
Phosphatidylserine(44:2)HMDB
1,2-Dierucoyl-rac-glycero-3-phosphoserineHMDB
1,2-Di(13Z-docosenoyl)-rac-glycero-3-phosphoserineHMDB
(2S)-2-Amino-3-({[(2R)-2,3-bis[(13Z)-docos-13-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoateHMDB
1-erucoyl-2-erucoyl-sn-glycero-3-phosphoserine SMPDB, HMDB
PS(22:1/22:1) SMPDB, HMDB
PS(22:1n9/22:1n9) SMPDB, HMDB
PS(22:1w9/22:1w9) SMPDB, HMDB
PS(44:2) SMPDB, HMDB
Pser(22:1(13Z)/22:1(13Z)) SMPDB, HMDB
Pser(22:1/22:1) SMPDB, HMDB
Pser(22:1n9/22:1n9) SMPDB, HMDB
Pser(22:1w9/22:1w9) SMPDB, HMDB
Pser(44:2) SMPDB, HMDB
Phosphatidylserine(22:1(13Z)/22:1(13Z)) SMPDB, HMDB
Phosphatidylserine(22:1/22:1) SMPDB, HMDB
Phosphatidylserine(22:1n9/22:1n9) SMPDB, HMDB
Phosphatidylserine(22:1w9/22:1w9) SMPDB, HMDB
PS(22:1(13Z)/22:1(13Z))SMPDB
Chemical FormulaC50H94NO10P
Average Molecular Weight900.27
Monoisotopic Molecular Weight899.6615
IUPAC Name(2S)-2-amino-3-({[(2R)-2,3-bis[(13Z)-docos-13-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Name(2S)-2-amino-3-{[(2R)-2,3-bis[(13Z)-docos-13-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)C(O)=O
InChI Identifier
InChI=1S/C50H94NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-48(52)58-43-46(44-59-62(56,57)60-45-47(51)50(54)55)61-49(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,46-47H,3-16,21-45,51H2,1-2H3,(H,54,55)(H,56,57)/b19-17-,20-18-/t46-,47+/m1/s1
InChI KeyCDSNLLWRUZIGDZ-HTBRLBQXSA-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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.88ALOGPS
logP14.1ChemAxon
logS-7.3ALOGPS
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 Count50ChemAxon
Refractivity254.28 m³·mol⁻¹ChemAxon
Polarizability110.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0000000999-cbeea328e3ecb57bcc582021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-0900000999-4676c747c04d02775d492021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-0900000999-4676c747c04d02775d492021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000109-355d4a7f939199b672b62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0001030916-64ea87db36be1c9d49512021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0001030911-300c11f183c0c82d6a322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-45c72d4790cc1240a9ae2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000000090-d1350e5ace3494eea9b32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kj-0003400090-bf68468d2cac5b1854522021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0000000169-74a868510fb2513500ea2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000029-86a2201f712f22e2fd1f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0090000331-c8c0baaada464e128edc2021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0112755
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB095725
KNApSAcK IDNot Available
Chemspider ID74876198
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131819924
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available