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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000272
Secondary Accession Numbers
  • HMDB00272
Metabolite Identification
Common NamePhosphoserine
DescriptionPhosphoserine is the phosphoric acid ester of the amino acid serine. It is found in essentially all living organisms ranging from microbes to plants to mammals. Phosphoserine is a component of many proteins as the result of posttranslational modifications to the native protein’s serine residue(s). The phosphorylation of the hydroxyl functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Free phosphoserine is found in many biofluids and likely arises from the proteolysis of proteins containing phosphoserine residues (PMID: 7693088 ).
Structure
Data?1582752120
Synonyms
ValueSource
(+)-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
Chemical FormulaC3H8NO6P
Average Molecular Weight185.0725
Monoisotopic Molecular Weight185.008923505
IUPAC Name(2S)-2-amino-3-(phosphonooxy)propanoic acid
Traditional Namephosphoserine
CAS Registry Number407-41-0
SMILES
N[C@@H](COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility71 mg/mLNot Available
LogPNot AvailableNot Available
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
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02u1-0930000000-c899f07d021f46de8c592014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02am-0980000000-224ebb540cc8cfeee7bf2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0k92-0943000000-2c96e781366647a38c1b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0rka-2965000000-6295c9d3aab0dbbdbe062014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02u1-0930000000-c899f07d021f46de8c592017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-02am-0980000000-224ebb540cc8cfeee7bf2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0k92-0943000000-2c96e781366647a38c1b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0rka-2965000000-6295c9d3aab0dbbdbe062017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052b-0943000000-925dbf1f579400fe12752017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03yl-0890000000-f853ba80cc56b6057d3e2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf11012016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9720000000-0c93ad0358d5840580e02017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9200000000-96d828cba6dd306d7a052021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b552012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f42012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-3900000000-0424244742b82164682f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9100000000-f86c85cff0432259c7642012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-997762f62b3a2e22b12b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4732d51a493c7bf13c292012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000000000-f653dafdf17fa74b83a52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000000000-f653dafdf17fa74b83a52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-3900000000-76c6900db1ecb22c9dc62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9100000000-f86c85cff0432259c7642017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kr-9000000000-25381bf668ede8881af02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9000000000-63cde6935414b6893a5f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c22017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac250442016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d17112016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e02016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f47712016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-68e2a2413db514aab39e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-5900000000-0165c58c1b2c713290ed2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9300000000-8c803e99e72e9cb599132021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17.0 +/- 3.0 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.2 +/- 1.7 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 0.9 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified<0.11 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified59.051 +/- 21.239 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified<0.11 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<0.113 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified<0.11 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified4.605 (1.645-7.566) umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
details
UrineDetected and Quantified<0.11 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.0 (0.53-3.28) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.0 (2.71-10.4) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<0.11 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified146.693 +/- 9.722 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB04522
Phenol Explorer Compound IDNot Available
FooDB IDFDB021926
KNApSAcK IDC00007287
Chemspider ID62074
KEGG Compound IDC01005
BioCyc ID3-P-SERINE
BiGG IDNot Available
Wikipedia Link3-phosphoserine
METLIN ID5270
PubChem Compound68841
PDB IDNot Available
ChEBI ID15811
Food Biomarker OntologyNot Available
VMH IDPSER_L
MarkerDB IDMDB00000131
References
Synthesis ReferenceBarruel, Elena Mery. Biosynthesis of phosphoserine in vitro. Anales Fac. Quim. y Farm. (1960), 12 228-33.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Molina JA, Jimenez-Jimenez FJ, Gomez P, Vargas C, Navarro JA, Orti-Pareja M, Gasalla T, Benito-Leon J, Bermejo F, Arenas J: Decreased cerebrospinal fluid levels of neutral and basic amino acids in patients with Parkinson's disease. J Neurol Sci. 1997 Sep 10;150(2):123-7. [PubMed:9268238 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  4. Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [PubMed:7693088 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
Reactions
Phosphoserine + Oxoglutaric acid → Phosphohydroxypyruvic acid + L-Glutamic aciddetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the last step in the biosynthesis of serine from carbohydrates. The reaction mechanism proceeds via the formation of a phosphoryl-enzyme intermediates.
Gene Name:
PSPH
Uniprot ID:
P78330
Molecular weight:
25007.49
Reactions
Phosphoserine + Water → L-Serine + Phosphatedetails