GABAReceptorInhibitorgabareceptorinhibitor

Phosphoserine

By rofalproject
Common Name

Phosphoserine Description

The phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particliarly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serines structure was established in 1902. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-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 (+)-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 PlasmenylserineMeSH

Chemical Formlia

C3H8NO6P Average Molecliar Weight

185.0725 Monoisotopic Molecliar Weight

185.008923505 IUPAC Name

(2S)-2-amino-3-(phosphonooxy)propanoic acid Traditional Name

phosphoserine CAS Registry Number

407-41-0 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 Key

BZQFBWGGLXLEPQ-REOHCLBHSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

L-alpha-amino acids Alternative Parents

  • Phosphoethanolamines
  • Monoalkyl phosphates
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organic oxides
  • Monoalkylamines
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • O-phosphoserine (CHEBI:15811 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Component of Glycine, serine and threonine metabolism

    • Application

    Not Available Cellliar locations

  • Cytoplasm (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point170 – 171 °CNot Available Boiling PointNot AvailableNot Available Water Solubility71 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility19.9 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity32.91 m3·mol-1ChemAxon Polarizability13.97 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02u1-0930000000-c899f07d021f46de8c59View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)splash10-02am-0980000000-224ebb540cc8cfeee7bfView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0k92-0943000000-2c96e781366647a38c1bView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (4 TMS)splash10-0rka-2965000000-6295c9d3aab0dbbdbe06View in MoNA Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b55View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-3900000000-0424244742b82164682fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9100000000-f86c85cff0432259c764View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-997762f62b3a2e22b12bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4732d51a493c7bf13c29View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00kf-9000000000-5d40f9a41d75ac08b4c2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000000000-f653dafdf17fa74b83a5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-000i-3900000000-76c6900db1ecb22c9dc6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00kr-9000000000-25381bf668ede8881af0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00di-9000000000-63cde6935414b6893a5fView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm (predicted from logP)

    • Biofluid Locations

  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine

    • Tissue Location

  • Prostate

    • Pathways

    Name SMPDB Link KEGG Link 3-Phosphoglycerate dehydrogenase deficiencySMP00721Not Available Dihydropyrimidine Dehydrogenase Deficiency (DHPD)SMP00179Not Available Dimethylglycine Dehydrogenase DeficiencySMP00242Not Available Dimethylglycine Dehydrogenase DeficiencySMP00484Not Available Glycine and Serine MetabolismSMP00004map00260 Hyperglycinemia, non-ketoticSMP00485Not Available Non Ketotic HyperglycinemiaSMP00223Not Available SarcosinemiaSMP00244Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified17.0 +/- 3.0 uMAdlit (>18 years old)FemaleNormal

  • 1550070

    • details Cerebrospinal Fluid (CSF)Detected and Quantified4.2 +/- 1.7 uMAdlit (>18 years old)BothNormal

  • Geigy Scientific …

    • details Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 0.9 uMAdlit (>18 years old)BothNormal

  • 9268238

    • details UrineDetected and Quantified59.051 +/- 21.239 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Normal

  • Mordechai, Hien, …

    • details UrineDetected and Quantified4.605 (1.645-7.566) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • details UrineDetected and Quantified2.0 (0.53-3.28) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 18004736

    • details UrineDetected and Quantified6.0 (2.71-10.4) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 18004736

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details 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

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021926 KNApSAcK ID

    Not Available Chemspider ID

    62074 KEGG Compound ID

    C01005 BioCyc ID

    3-P-SERINE BiGG ID

    Not Available Wikipedia Link

    Phosphoserine NuGOwiki Link

    HMDB00272 Metagene Link

    HMDB00272 METLIN ID

    5270 PubChem Compound

    68841 PDB ID

    SEP ChEBI ID

    15811

    Product: Hyaluronic acid

    References Synthesis Reference Barruel, 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. 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 ]
    2. 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 Parkinsons disease. J Neurol Sci. 1997 Sep 10;150(2):123-7. [PubMed:9268238 ]

    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 acid details
    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 + Phosphoric acid details

    PMID: 16162000

    By rofalproject

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