Record Information
Version1.0
Creation date2011-09-21 00:05:17 UTC
Update date2020-09-17 15:38:31 UTC
Primary IDFDB021926
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Phosphoserine
DescriptionPhosphoserine, also known as dexfosfoserine or fosforina, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. The L-enantiomer of O-phosphoserine. Phosphoserine is a very strong basic compound (based on its pKa). Phosphoserine exists in all living species, ranging from bacteria to humans. Within humans, phosphoserine participates in a number of enzymatic reactions. In particular, phosphoserine and oxoglutaric acid can be biosynthesized from phosphohydroxypyruvic acid and L-glutamic acid; which is catalyzed by the enzyme phosphoserine aminotransferase. In addition, phosphoserine can be converted into L-serine; which is mediated by the enzyme phosphoserine phosphatase. In humans, phosphoserine is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway.
CAS Number407-41-0
Structure
Thumb
Synonyms
SynonymSource
(+)-L-Serine dihydrogen phosphate (ester)ChEBI
(2S)-2-Amino-3-(phosphonooxy)propanoic acidChEBI
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphateChEBI
3-PhosphoserineChEBI
DexfosfoserineChEBI
L-O-PhosphoserineChEBI
O-PhosphoserineChEBI
3-Phospho-L-serineKegg
(+)-L-Serine dihydrogen phosphoric acid (ester)Generator
(2S)-2-Amino-3-(phosphonooxy)propanoateGenerator
(S)-2-Amino-3-hydroxypropanoate 3-phosphateGenerator
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acidGenerator
3-O-PhosphoserineHMDB
FosforinaHMDB
L-3-PhosphoserineHMDB
L-O-Serine phosphateHMDB
L-PhosphoserineHMDB
L-Serine dihydrogen phosphate (ester)HMDB
L-Serine phosphateHMDB
L-SerinephosphorateHMDB
L-Serinephosphoric acidHMDB
L-Seryl phosphateHMDB
PlasmenylserineHMDB
(+)-L-Serine dihydrogen ate (ester)ChEBI
(+)-L-Serine dihydrogen ic acid (ester)Generator
(2S)-2-amino-3-(Onooxy)propanoateGenerator
(2S)-2-amino-3-(Onooxy)propanoic acidChEBI
(S)-2-amino-3-Hydroxypropanoate 3-ateGenerator
(S)-2-amino-3-Hydroxypropanoic acid 3-ateChEBI
(S)-2-amino-3-Hydroxypropanoic acid 3-ic acidGenerator
3-O-OserineHMDB
3-OserineChEBI
Dexfosfoserine, INNdb_source
L-3-OserineHMDB
L-O-OserineChEBI
L-O-Serine ateHMDB
L-OserineHMDB
L-Serine ateHMDB
L-Serine dihydrogen ate (ester)HMDB
L-SerineorateHMDB
L-Serineoric acidHMDB
L-Seryl ateHMDB
O-O-L-SerineChEBI
O-OserineChEBI
OserineChEBI
S-Phosphoserinemanual
Predicted Properties
PropertyValueSource
Water Solubility19.9 g/LALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)1.2ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability13.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H8NO6P
IUPAC name(2S)-2-amino-3-(phosphonooxy)propanoic acid
InChI IdentifierInChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
InChI KeyBZQFBWGGLXLEPQ-REOHCLBHSA-N
Isomeric SMILESN[C@@H](COP(O)(O)=O)C(O)=O
Average Molecular Weight185.0725
Monoisotopic Molecular Weight185.008923505
Classification
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02u1-0930000000-c899f07d021f46de8c59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02am-0980000000-224ebb540cc8cfeee7bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0k92-0943000000-2c96e781366647a38c1bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0rka-2965000000-6295c9d3aab0dbbdbe06JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02u1-0930000000-c899f07d021f46de8c59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02am-0980000000-224ebb540cc8cfeee7bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0k92-0943000000-2c96e781366647a38c1bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0rka-2965000000-6295c9d3aab0dbbdbe06JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0943000000-925dbf1f579400fe1275JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03yl-0890000000-f853ba80cc56b6057d3eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf1101JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9720000000-0c93ad0358d5840580e0JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b55JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-3900000000-0424244742b82164682fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9100000000-f86c85cff0432259c764JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-997762f62b3a2e22b12bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4732d51a493c7bf13c29JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000000000-f653dafdf17fa74b83a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000000000-f653dafdf17fa74b83a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-76c6900db1ecb22c9dc6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9100000000-f86c85cff0432259c764JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9000000000-25381bf668ede8881af0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-63cde6935414b6893a5fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac25044JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d1711JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f4771JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID62074
ChEMBL IDCHEMBL284377
KEGG Compound IDC01005
Pubchem Compound ID68841
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB04522
HMDB IDHMDB00272
CRC / DFC (Dictionary of Food Compounds) IDCJC00-O:CJC02-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSEP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoserine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphoserine aminotransferasePSAT1Q9Y617
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference