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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:21 UTC
Update Date2017-10-23 19:03:53 UTC
HMDB IDHMDB0001721
Secondary Accession Numbers
  • HMDB01721
Metabolite Identification
Common NameDL-O-Phosphoserine
DescriptionIt is a normal metabolite found in human biofluids. (PMID 7693088 , 7688003 ). The phosphoric ester of serine. -- Pubchem. Serine 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. - Wikipedia.
Structure
Thumb
Synonyms
ValueSource
2-amino-3-(Phosphonooxy)propanoic acidChEBI
DL-Serine dihydrogen phosphateChEBI
DL-Serine, dihydrogen phosphate (ester)ChEBI
PhosphoserineChEBI
2-amino-3-(Phosphonooxy)propanoateGenerator
DL-Serine dihydrogen phosphoric acidGenerator
DL-Serine, dihydrogen phosphoric acid (ester)Generator
3-phospho-1-SerineHMDB
3-phospho-SerineHMDB
3-PhosphoserineHMDB
DL-O-PhosphorylserineHMDB
DL-O-Serine phosphateHMDB
DL-Serine monophosphorateHMDB
DL-Serine monophosphoric acidHMDB
EnergoserinaHMDB
O-phospho-DL-SerineHMDB
O-phospho-L-SerineHMDB
O-PhosphonoserineHMDB
P-SerineHMDB
PhosphorylserineHMDB
Serine phosphateHMDB
Serine-3-phosphateHMDB
SerophenHMDB
Phosphate, serylMeSH
Seryl phosphateMeSH
Phosphate, serineMeSH
Chemical FormulaC3H8NO6P
Average Molecular Weight185.0725
Monoisotopic Molecular Weight185.008923505
IUPAC Name2-amino-3-(phosphonooxy)propanoic acid
Traditional NameP-serine
CAS Registry Number17885-08-4
SMILES
NC(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)
InChI KeyBZQFBWGGLXLEPQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf1101View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6900000000-fbaee5e7f89c1dcb6669View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-9000000000-64c49953b5b27ea372c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9300000000-2adf6419e88c778446e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9200000000-04bb0aee57d7fffbcaa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac25044View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d1711View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f4771View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Epidermis
  • Testes
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified1.05 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.33 +/- 0.001 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022700
    KNApSAcK IDNot Available
    Chemspider ID104
    KEGG Compound IDC01005
    BioCyc ID3-P-SERINE
    BiGG ID36594
    Wikipedia Link3-phosphoserine
    METLIN ID6338
    PubChem Compound106
    PDB IDNot Available
    ChEBI ID37712
    References
    Synthesis ReferenceLacombe J M; Andriamanampisoa F; Pavia A A Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group. International journal of peptide and protein research (1990), 36(3), 275-80.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Glaus M, Schneider W: Iron release from transferrin induced by mixed ligand complexes of copper(II). Biol Met. 1989;2(3):185-90. [PubMed:2490073 ]
    2. Driscoll J, Zuo Y, Xu T, Choi JR, Troxler RF, Oppenheim FG: Functional comparison of native and recombinant human salivary histatin 1. J Dent Res. 1995 Dec;74(12):1837-44. [PubMed:8600179 ]
    3. 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 ]
    4. Wishart MJ, Denu JM, Williams JA, Dixon JE: A single mutation converts a novel phosphotyrosine binding domain into a dual-specificity phosphatase. J Biol Chem. 1995 Nov 10;270(45):26782-5. [PubMed:7592916 ]
    5. Patten BM, Harati Y, Acosta L, Jung SS, Felmus MT: Free amino acid levels in amyotrophic lateral sclerosis. Ann Neurol. 1978 Apr;3(4):305-9. [PubMed:666270 ]
    6. Etheredge RE, Han S, Fossel E, Tanzer ML, Glimcher MJ: Identification and quantitation of O-phosphoserine in human plasma fibronectin. FEBS Lett. 1985 Jul 8;186(2):259-62. [PubMed:3924662 ]
    7. Pond CD, Leachman SA, Warters RL: Accumulation, activation and interindividual variation of the epidermal TP53 protein in response to ionizing radiation in organ cultured human skin. Radiat Res. 2004 Jun;161(6):739-45. [PubMed:15161345 ]
    8. Partsch G, Schwarzer C, Eberl R: Influence of anticoagulant substances on phosphoserine and taurine of human blood. Arzneimittelforschung. 1979;29(5):820-2. [PubMed:115479 ]
    9. Millan JL, Whyte MP, Avioli LV, Fishman WH: Hypophosphatasia (adult form): quantitation of serum alkaline phosphatase isoenzyme activity in a large kindred. Clin Chem. 1980 Jun;26(7):840-5. [PubMed:7379306 ]
    10. Kataoka H, Nakai K, Makita M: Identification of O-phosphoamino acids in urine hydrolysate by gas chromatography-mass spectrometry. J Chromatogr. 1993 May 19;615(1):136-41. [PubMed:7688003 ]

    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
    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