Canmetcon
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Identification
YMDB IDYMDB00761
NameO-Phospho-L-serine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionO-Phospho-L-serine is an intermediate in serine biosynthesis pathway. Serine is an important precursor used for the biosynthesis of glycine, cysteine, tryptophan, and phospholipids. [Biocyc SERSYN-PWY]
Structure
Thumb
Synonyms
  • (+)-L-serine dihydrogen phosphate (ester)
  • (2S)-2-amino-3-(phosphonooxy)propanoic acid
  • (S)-2-amino-3-hydroxypropanoic acid 3-phosphate
  • 3-O-Phosphoserine
  • 3-phosphoserine
  • Dexfosfoserine
  • Fosforina
  • L-3-Phosphoserine
  • L-O-Phosphoserine
  • L-O-Serine phosphate
  • L-Phosphoserine
  • L-Serine dihydrogen phosphate (ester)
  • L-Serine phosphate
  • L-Serinephosphorate
  • L-Serinephosphoric acid
  • L-Seryl phosphate
  • O-Phospho-L-serine
  • O-phosphoserine
  • phosphoserine
  • 3-Phospho-L-serine
  • (+)-L-Serine dihydrogen phosphoric acid (ester)
  • (2S)-2-Amino-3-(phosphonooxy)propanoate
  • (S)-2-Amino-3-hydroxypropanoate 3-phosphate
  • (S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid
  • Plasmenylserine
CAS number407-41-0
WeightAverage: 185.0725
Monoisotopic: 185.008923505
InChI KeyBZQFBWGGLXLEPQ-REOHCLBHSA-N
InChIInChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
IUPAC Name(2S)-2-amino-3-(phosphonooxy)propanoic acid
Traditional IUPAC Namephosphoserine
Chemical FormulaC3H8NO6P
SMILESN[C@@H](COP(O)(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-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
StateSolid
Charge0
Melting point170-171 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability13.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Glycine, serine and threonine metabolismec00260 Map00260
Methane metabolismec00680 Map00680
SMPDB ReactionsNot Available
KEGG Reactions
O-Phospho-L-serine + waterL-Serine + phosphate
Phosphohydroxypyruvic acid + L-Glutamic acidO-Phospho-L-serine + Oxoglutaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Belhumeur, P., Fortin, N., Clark, M. W. (1994). "A gene from Saccharomyces cerevisiae which codes for a protein with significant homology to the bacterial 3-phosphoserine aminotransferase." Yeast 10:385-389.8017107
  • Melcher, K., Entian, K. D. (1992). "Genetic analysis of serine biosynthesis and glucose repression in yeast." Curr Genet 21:295-300.1326413
Synthesis Reference:Barruel, Elena Mery. Biosynthesis of phosphoserine in vitro. Anales Fac. Quim. y Farm. (1960), 12 228-33.
External Links:
ResourceLink
CHEBI ID15811
HMDB IDHMDB00272
Pubchem Compound ID68841
Kegg IDC01005
ChemSpider ID62074
FOODB IDFDB021926
WikipediaPhosphoserine
BioCyc ID3-P-SERINE

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
Gene Name:
SER1
Uniprot ID:
P33330
Molecular weight:
43415.19922
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.
General function:
Involved in catalytic activity
Specific function:
O-phospho-L(or D)-serine + H(2)O = L(or D)- serine + phosphate
Gene Name:
SER2
Uniprot ID:
P42941
Molecular weight:
34207.0
Reactions
O-phospho-L(or D)-serine + H(2)O → L(or D)-serine + phosphate.