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O-Phospho-D-serine (M2MDB001116)

Record Information
Version2.0
Creation Date2012-05-31 14:36:46 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB20276
Identification
Name:O-Phospho-D-serine
DescriptionO-phospho-D-serine is a phosphoric ester of serine and phosphoric acid. Phosphorylated serine residues are often referred to as phosphoserine. Phosphoserine is a component of many proteins. The phosphorylation of the alcohol functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Free phosphoserine may be found after proteins have been proteolyzed. Phosphoserine phosphatase is able to dephosphorylate phosphoserince (both L and D forms).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-2-amino-3-phosphonooxypropanoate
  • (2S)-2-amino-3-phosphonooxypropanoic acid
  • 2-Amino-3-(phosphonooxy)propanoate
  • 2-Amino-3-(phosphonooxy)propanoic acid
  • 3-P-Serine
  • 3-Phospho-1-serine
  • 3-Phospho-L-serine
  • 3-Phospho-serine
  • 3-Phosphoserine
  • D -2-Amino-3-hydroxypropanoate 3-phosphate
  • D -2-Amino-3-hydroxypropanoic acid 3-phosphate
  • D -2-amino-3-Hydroxypropanoic acid 3-phosphoric acid
  • D-O-Phosphoserine
  • DL-2-Amino-3-hydroxypropanoate 3-phosphate
  • DL-2-Amino-3-hydroxypropanoic acid 3-phosphate
  • DL-2-amino-3-Hydroxypropanoic acid 3-phosphoric acid
  • DL-O-phosphorylserine
  • DL-O-phosphoserine
  • DL-O-serine phosphate
  • DL-O-Serine phosphoric acid
  • DL-phosphoserine
  • DL-serine dihydrogen phosphate
  • DL-Serine dihydrogen phosphoric acid
  • DL-Serine monophosphate
  • DL-serine monophosphorate
  • DL-serine monophosphoric acid
  • DL-serine, dihydrogen phosphate (ester)
  • DL-Serine, dihydrogen phosphoric acid (ester)
  • DL-sop
  • Energoserina
  • L-Serine, dihydrogen phosphate
  • L-Serine, dihydrogen phosphoric acid
  • O-Phospho-DL-serine
  • O-Phospho-L-serine
  • O-Phosphono-Serine
  • O-Phosphonoserine
  • O-Phosphoserine
  • P-Ser
  • P-Serine
  • Phosphonoserine
  • Phosphorylserine
  • Phosphoserine
  • Serine phosphate
  • Serine phosphoric acid
  • Serine, dihydrogen phosphate (ester) (9CI)
  • Serine, dihydrogen phosphate (ester), DL- (8CI)
  • Serine, dihydrogen phosphoric acid (ester) (9ci)
  • Serine, dihydrogen phosphoric acid (ester), DL- (8ci)
  • Serine-3-p
  • Serine-3-phosphate
  • Serine-3-phosphoric acid
  • Serophen
  • Seryl phosphate
  • Seryl phosphoric acid
  • [1-14c] Serine Dihydrogen Phosphate (ester)
  • [1-14C] Serine dihydrogen phosphoric acid (ester)
Chemical Formula:C3H8NO6P
Weight:Average: 185.0725
Monoisotopic: 185.008923505
InChI Key:BZQFBWGGLXLEPQ-UWTATZPHSA-N
InChI: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-/m1/s1
CAS number:17885-08-4
IUPAC Name:(2R)-2-amino-3-(phosphonooxy)propanoic acid
Traditional IUPAC Name:O-phospho-D-serine
SMILES:[H][C@@](N)(COP(O)(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-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
Physical Properties
State:Solid
Charge:-2
Melting point:228 °C
Experimental Properties:
PropertyValueSource
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
Polarizability14.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
O-Phospho-D-serine + Water > L-Serine + Inorganic phosphate
Phosphoserine + O-Phospho-D-serine + Water <> L-Serine + D-Serine + Phosphate
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-8900000000-fa80206f357e691b1927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-db6b02072c0568e8e773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b3fe18e3e231ec92a4b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003s-8900000000-1624d6cd2551f1de721bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-6eb41a3603612c36a612View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-cb44ff87fe2054851088View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-5900000000-0165c58c1b2c713290edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9300000000-8c803e99e72e9cb59913View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9000000000-6ed59f8b5f83d923a8b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-68e2a2413db514aab39eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID37713
HMDB IDHMDB0304154
Pubchem Compound ID106
Kegg IDC02532
ChemSpider ID388807
Wikipedia IDNot Available
BioCyc IDCPD-3722
EcoCyc IDCPD-3722

Enzymes

Protein Details
1. Phosphoserine phosphatase
General function:
Involved in catalytic activity
Specific function:
O-phospho-L(or D)-serine + H(2)O = L(or D)- serine + phosphate
Gene Name:
serB
Uniprot ID:
P0AGB0
Molecular weight:
35042
Reactions
O-phospho-L(or D)-serine + H(2)O = L(or D)-serine + phosphate.