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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Phosphoserine, x TMS, GC-MS Spectrumsplash10-02u1-0930000000-c899f07d021f46de8c59Spectrum
GC-MSL-Phosphoserine, x TMS, GC-MS Spectrumsplash10-02am-0980000000-224ebb540cc8cfeee7bfSpectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-0k92-0943000000-2c96e781366647a38c1bSpectrum
GC-MSL-Phosphoserine, 4 TMS, GC-MS Spectrumsplash10-0rka-2965000000-6295c9d3aab0dbbdbe06Spectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-02u1-0930000000-c899f07d021f46de8c59Spectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-02am-0980000000-224ebb540cc8cfeee7bfSpectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-0k92-0943000000-2c96e781366647a38c1bSpectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-0rka-2965000000-6295c9d3aab0dbbdbe06Spectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-052b-0943000000-925dbf1f579400fe1275Spectrum
GC-MSL-Phosphoserine, non-derivatized, GC-MS Spectrumsplash10-03yl-0890000000-f853ba80cc56b6057d3eSpectrum
Predicted GC-MSL-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf1101Spectrum
Predicted GC-MSL-Phosphoserine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9720000000-0c93ad0358d5840580e0Spectrum
Predicted GC-MSL-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Phosphoserine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b552012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-3900000000-0424244742b82164682f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9100000000-f86c85cff0432259c7642012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-997762f62b3a2e22b12b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4732d51a493c7bf13c292012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000000000-f653dafdf17fa74b83a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000000000-f653dafdf17fa74b83a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-76c6900db1ecb22c9dc62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9100000000-f86c85cff0432259c7642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9000000000-25381bf668ede8881af02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-63cde6935414b6893a5f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-030fc19bab74121b95362021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-78dc68824c37b96fd97f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8c715ebc5361358f572d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000t-5900000000-2acd16447bafd738b8b22021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac250442016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d17112016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f47712016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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