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Record Information
Version3.6
Creation Date2005-11-20 22:13:21 UTC
Update Date2016-02-11 01:04:59 UTC
HMDB IDHMDB01721
Secondary Accession NumbersNone
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
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 KeyInChIKey=BZQFBWGGLXLEPQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycine, serine and threonine metabolism
  • Component of Vitamin B6 metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 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
Polarizability14.01 Å3ChemAxon
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-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Epidermis
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB01721
Metagene LinkHMDB01721
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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