DL-O-Phosphoserine (CHEM021783)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:24 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021783
Identification
Common NameDL-O-Phosphoserine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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, serylHMDB
Seryl phosphateHMDB
Phosphate, serineHMDB
Chemical FormulaC3H8NO6P
Average Molecular Mass185.073 g/mol
Monoisotopic Mass185.009 g/mol
CAS Registry Number17885-08-4
IUPAC Name2-amino-3-(phosphonooxy)propanoic acid
Traditional NameP-serine
SMILESNC(COP(O)(O)=O)C(O)=O
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)
InChI KeyBZQFBWGGLXLEPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf1101Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6900000000-fbaee5e7f89c1dcb6669Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b55Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-9000000000-64c49953b5b27ea372c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9300000000-2adf6419e88c778446e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9200000000-04bb0aee57d7fffbcaa7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9100000000-2fb2869ecf3634b54a39Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9000000000-2c6e3412bb661c65ec10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac25044Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d1711Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f4771Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-5900000000-0165c58c1b2c713290edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9300000000-8c803e99e72e9cb59913Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9000000000-6ed59f8b5f83d923a8b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-68e2a2413db514aab39eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001721
FooDB IDFDB022700
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID36594
BioCyc IDNot Available
METLIN ID6338
PDB IDNot Available
Wikipedia LinkPhosphoserine
Chemspider ID104
ChEBI ID37712
PubChem Compound ID106
Kegg Compound IDC01005
YMDB IDYMDB00076
ECMDB IDECMDB24073
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lacombe 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.
2. Lacombe 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.
3. 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.
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.
5. 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.
6. 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.
7. 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.
8. 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.
9. Partsch G, Schwarzer C, Eberl R: Influence of anticoagulant substances on phosphoserine and taurine of human blood. Arzneimittelforschung. 1979;29(5):820-2.
10. Glaus M, Schneider W: Iron release from transferrin induced by mixed ligand complexes of copper(II). Biol Met. 1989;2(3):185-90.
11. 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.
12. 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.
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=7693088