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DL-O-Phosphoserine (M2MDB006190)

Record Information
Version2.0
Creation Date2015-09-08 17:48:57 -0600
Update Date2015-09-08 17:48:57 -0600
Secondary Accession Numbers
  • ECMDB24073
Identification
Name:DL-O-Phosphoserine
Description
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 Formula:C3H8NO6P
Weight:Average: 185.0725
Monoisotopic: 185.008923505
InChI Key:BZQFBWGGLXLEPQ-UHFFFAOYSA-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)
CAS number:Not Available
IUPAC Name:2-amino-3-(phosphonooxy)propanoic acid
Traditional IUPAC Name:P-serine
SMILES:NC(COP(O)(O)=O)C(O)=O
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
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
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
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphohydroxypyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + DL-O-Phosphoserine
DL-O-Phosphoserine + Water > Phosphate + L-Serine + L-Serine
Adenosine triphosphate + Water + DL-O-Phosphoserine > Hydrogen ion + Phosphate + Adenosine diphosphate + DL-O-Phosphoserine + ADP
Adenosine triphosphate + Water + DL-O-Phosphoserine > Hydrogen ion + Phosphate + Adenosine diphosphate + DL-O-Phosphoserine + ADP
SMPDB Pathways:
Secondary Metabolites: cysteine biosynthesis from serinePW000977 ThumbThumb?image type=greyscaleThumb?image type=simple
cysteine biosynthesisPW000800 ThumbThumb?image type=greyscaleThumb?image type=simple
serine biosynthesis and metabolismPW000809 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9100000000-2fb2869ecf3634b54a39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9000000000-2c6e3412bb661c65ec10View 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
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 NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID37712
HMDB IDHMDB0001721
Pubchem Compound ID106
Kegg IDC01005
ChemSpider ID104
Wikipedia IDPhosphoserine
BioCyc IDNot Available

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.
Protein Details
2. Phosphoserine aminotransferase
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. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Uniprot ID:
P23721
Molecular weight:
39783
Reactions
O-phospho-L-serine + 2-oxoglutarate = 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate = (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.
Protein Details
3. Phosphonates import ATP-binding protein PhnC
General function:
Inorganic ion transport and metabolism
Specific function:
Part of the ABC transporter complex PhnCDE involved in phosphonates, phosphate esters, phosphite and phosphate import. Responsible for energy coupling to the transport system
Gene Name:
phnC
Uniprot ID:
P16677
Molecular weight:
29430
Reactions
ATP + H(2)O + phosphonate(Out) = ADP + phosphate + phosphonate(In).

Transporters

Protein Details
1. Putative phosphonates transport system permease protein phnE
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for phosphonates; probably responsible for the translocation of the substrate across the membrane
Gene Name:
phnE
Uniprot ID:
P16683
Molecular weight:
28383
Protein Details
2. Phosphonates import ATP-binding protein PhnC
General function:
Inorganic ion transport and metabolism
Specific function:
Part of the ABC transporter complex PhnCDE involved in phosphonates, phosphate esters, phosphite and phosphate import. Responsible for energy coupling to the transport system
Gene Name:
phnC
Uniprot ID:
P16677
Molecular weight:
29430
Reactions
ATP + H(2)O + phosphonate(Out) = ADP + phosphate + phosphonate(In).
Protein Details
3. Phosphonates-binding periplasmic protein
General function:
alkylphosphonate transport
Specific function:
Phosphonate binding protein that is part of the phosphonate uptake system. Exhibits high affinity for 2-aminoethylphosphonate, and somewhat less affinity to ethylphosphonate, methylphosphonate, phosphonoacetate and phenylphosphonate.
Gene Name:
phnD
Uniprot ID:
P16682
Molecular weight:
37370