Page last updated: 2024-11-04

phosphoserine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Phosphoserine: The phosphoric acid ester of serine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID106
CHEMBL ID180002
CHEBI ID37712
SCHEMBL ID6847
MeSH IDM0016735

Synonyms (64)

Synonym
nsc90791
nsc-90791
phosphoserine
phosphorylserine
serine phosphate
dl-serine dihydrogen phosphate
seryl phosphate
dl-serine, dihydrogen phosphate (ester)
p-serine
o-phospho-dl-serine
dl-o-phosphorylserine
3-phospho-serine
p-ser
serine-3-p
serine-3-phosphate
dl-serine monophosphoric acid
dl-sop
serine, o-phosphono-
energoserina
dl-2-amino-3-hydroxypropanoic acid 3-phosphate
dl-o-serine phosphate
dl-o-phosphoserine
dl-phosphoserine
serophen
serine, dihydrogen phosphate (ester), dl- (8ci)
3-phospho-1-serine
serine, dihydrogen phosphate (ester) (9ci)
3-P-SERINE ,
17885-08-4
2-amino-3-(phosphonooxy)propanoic acid
CHEBI:37712 ,
o-phosphonoserine
o-phospho-dl-serine, >=98.0% (nt)
phosphoserine, dl-
L000353
FT-0695862
FT-0695863
CHEMBL180002
2-amino-3-phosphonooxypropanoic acid
nsc 90791
einecs 241-834-7
unii-6gv29p6oza
6gv29p6oza ,
AKOS015998288
2-amino-3-(oxyphosphinyloxyphosphinyl)propanoic acid
FT-0625495
FT-0628015
SCHEMBL6847
(rs)-2-amino-3-phosphonooxy propanoic acid
serine, dihydrogen phosphate (ester), dl-
serine phosphate [who-dd]
BZQFBWGGLXLEPQ-UHFFFAOYSA-N
mfcd00021723
dl-serine monophosphorate
o-phosphoserin
sr-01000075466
SR-01000075466-1
h-d-ser(poh)-oh
h-ser(poh)-oh
HY-15130
CS-0003781
h-dl-ser(h2po3)-oh
F82024
DTXSID00859358

Research Excerpts

Overview

L-Phosphoserine is a membrane metabolite that is elevated in Alzheimer's disease brain.

ExcerptReferenceRelevance
"L-Phosphoserine is a membrane metabolite that is elevated in Alzheimer's disease brain. "( Possible roles of L-phosphoserine in the pathogenesis of Alzheimer's disease.
Klunk, WE; McClure, RJ; Pettegrew, JW, 1991
)
1.33

Effects

Phosphoserine (pSer) has a natural role in biomineralization. Has potential effectiveness as a simple substrate in preparing bone replacement materials, which could enhance bone forming ability.

ExcerptReferenceRelevance
"Phosphoserine (pSer), which has a natural role in biomineralization, has been identified to possess the functionality to react with calcium phosphate phases, such as tetracalcium phosphate (TTCP) and α-tricalcium phosphate (α-TCP), and form a uniquely adhesive cement."( Identification of a calcium phosphoserine coordination network in an adhesive organo-apatitic bone cement system.
Baker, I; Kesseli, FP; Lauer, CS; Mirica, KA; Van Citters, DW, 2020
)
1.57
"Phosphoserine (pSer), which has a natural role in biomineralization, has been identified to possess the functionality to react with calcium phosphate phases, such as tetracalcium phosphate (TTCP) and α-tricalcium phosphate (α-TCP), and form a uniquely adhesive cement."( Identification of a calcium phosphoserine coordination network in an adhesive organo-apatitic bone cement system.
Baker, I; Kesseli, FP; Lauer, CS; Mirica, KA; Van Citters, DW, 2020
)
1.57
"Phosphoserine has potential effectiveness as a simple substrate in preparing bone replacement materials, which could enhance bone forming ability. "( Phosphoserine promotes osteogenic differentiation of human adipose stromal cells through bone morphogenetic protein signalling.
Chen, H; Chen, X; Cheng, S; Guo, X; Xu, HZ; Ying, X, 2014
)
3.29
"Phosphoserine has been shown to be the phosphorylated amino acid in myosin IB."( Purification and characterization of a myosin I heavy chain kinase from Acanthamoeba castellanii.
Albanesi, JP; Hammer, JA; Korn, ED, 1983
)
0.99
"Phosphoserine peptides have been isolated by a diagonal electrophoresis method from proteolytic digests of ovalbumins from hen, grouse, turkey, golden pheasant, magpie goose, chinese goose, Aylesbury duck and fulvous whistling duck. "( Sequences of sixteen phosphoserine peptides from ovalbumins of eight species.
Fothergill, JE; Fothergill, LA; Henderson, JY; Moir, AJ, 1981
)
2.02
"L-Phosphoserine has also been found to be a competitive antagonist at the N-methyl-D-aspartate recognition site and an antagonist of metabotropic receptor-mediated hydrolysis of inositol phospholipids."( Possible roles of L-phosphoserine in the pathogenesis of Alzheimer's disease.
Klunk, WE; McClure, RJ; Pettegrew, JW, 1991
)
1.16

Toxicity

ExcerptReferenceRelevance
" The biocompatibility of synthesized segmented polyurethanes was then investigated by platelet-rich plasma contact studies and related scanning electron microscopy (SEM) photographs for blood compatibility and cytotoxicity assay (MTT test) on material elution to assess the effect of any toxic leachables on cellular viability."( Synthesis, platelet adhesion and cytotoxicity studies of new glycerophosphoryl-containing polyurethanes.
D'Arrigo, P; Giordano, C; Macchi, P; Malpezzi, L; Pedrocchi-Fantoni, G; Servi, S, 2007
)
0.34
" Involvement of p66shc in adverse effects of these drugs was determined in p66shc knockdown, Ser36 phosphorylation (S36A) and cytochrome c-binding (W134F)- deficient cells."( The role of p66shc in taxol- and dichloroacetic acid-dependent renal toxicity.
Arany, I; Clark, JS; Ember, I; Juncos, LA; Reed, D; Szabó, I, 2013
)
0.39
" Knockdown of p66shc, mutation of its Ser36 (S36A) or cytochrome c binding site (W134F) attenuated adverse effects of the two drugs."( The role of p66shc in taxol- and dichloroacetic acid-dependent renal toxicity.
Arany, I; Clark, JS; Ember, I; Juncos, LA; Reed, D; Szabó, I, 2013
)
0.39
"Taxol and DCA are potentially nephrotoxic owing their adverse effects on activation of p66shc."( The role of p66shc in taxol- and dichloroacetic acid-dependent renal toxicity.
Arany, I; Clark, JS; Ember, I; Juncos, LA; Reed, D; Szabó, I, 2013
)
0.39

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic behaviour of the various active ingredients was examined at a haematic level."( Pharmacokinetic study of the relative bioavailability and bioequivalence after oral intensive or repeated short term treatment with two polyamino acid formulations.
Castana, R; Insirello, L; Leonardi, G; Matera, M, 1993
)
0.29

Bioavailability

ExcerptReferenceRelevance
"The phosphorylation of insulin-like growth factor binding protein-I (IGFBP-1) alters its binding affinity for insulin-like growth factor I (IGF-I) and thus regulates the bioavailability of IGF-I for binding to the IGF-I receptor."( Characterization of insulin-like growth factor binding protein-1 kinases from human hepatoma cells.
Ankrapp, DP; Clemmons, DR; Jones, JI, 1996
)
0.29
" First, we evaluated the responses of human cells to microwave exposure at a specific absorption rate (SAR) of 80 mW/kg, which corresponds to the limit of the average whole-body SAR for general public exposure defined as a basic restriction in the International Commission on Non-Ionizing Radiation Protection (ICNIRP) guidelines."( Mobile phone base station-emitted radiation does not induce phosphorylation of Hsp27.
Hirose, H; Inoue, K; Kaji, N; Miyakoshi, J; Nakayama, K; Nojima, T; Sakuma, N; Sekijima, M, 2007
)
0.34
" Growth factors increase locomotor activity in both PD and aging models and increase DA bioavailability and ser31 TH phosphorylation in SN, suggesting that ser31 TH phosphorylation status in the SN, not striatum, regulates DA bioavailability necessary for locomotor activity."( Aging reveals a role for nigral tyrosine hydroxylase ser31 phosphorylation in locomotor activity generation.
Dempsey, C; Pruett, BS; Salvatore, MF; Spann, SL, 2009
)
0.35
"Together, these results show ser31 TH phosphorylation regulates DA bioavailability in intact neuropil, its status in the SN may regulate locomotor activity generation, and it may represent an accurate target for treating locomotor deficiency."( Aging reveals a role for nigral tyrosine hydroxylase ser31 phosphorylation in locomotor activity generation.
Dempsey, C; Pruett, BS; Salvatore, MF; Spann, SL, 2009
)
0.35
" Thus, to the extent that somatodendritic DA release affects behavior, TH regulation in the midbrain may be critical for DA bioavailability to influence behavior."( Dichotomy of tyrosine hydroxylase and dopamine regulation between somatodendritic and terminal field areas of nigrostriatal and mesoaccumbens pathways.
Pruett, BS; Salvatore, MF, 2012
)
0.38
" This study provides novel understanding of the cellular mechanism that controls fetal IGFBP-1 phosphorylation in hypoxia, and we propose that mTOR inhibition constitutes a mechanistic link between hypoxia, reduced IGF-I bioavailability and FGR."( Hypoxia Increases IGFBP-1 Phosphorylation Mediated by mTOR Inhibition.
Abu Shehab, M; Biggar, KK; Damerill, I; Gupta, MB; Jansson, T; Li, SS, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves of PMA and of forskolin for the inhibition of PLC-gamma 1 tyrosine phosphorylation and of PtdIns 4,5-P2 hydrolysis were similar."( Inhibition of CD3-linked phospholipase C by phorbol ester and by cAMP is associated with decreased phosphotyrosine and increased phosphoserine contents of PLC-gamma 1.
Min, HK; Park, DJ; Rhee, SG, 1992
)
0.49
" Here we show that complex formation between CBP and RNA polymerase II requires RNA helicase A (RHA), a nuclear DNA/RNA helicase that is related to the Drosophila male dosage compensation factor mle."( RNA helicase A mediates association of CBP with RNA polymerase II.
Anderson, SF; Hurwitz, J; Lee, CG; Montminy, M; Nakajima, T; Parvin, JD; Uchida, C, 1997
)
0.3
" H-89, per se, did not modify glutamate release but reduced extracellular GABA value at the higher dosage used (200 microM)."( Differential roles of mGlu8 receptors in the regulation of glutamate and gamma-aminobutyric acid release at periaqueductal grey level.
de Novellis, V; Maione, S; Marabese, I; Mariani, L; Palazzo, E; Rodella, L; Rossi, F; Siniscalco, D, 2005
)
0.33
" elegans specific dosage complex can be phosphorylated on most subunits, suggesting its regulation by kinases."( Caenorhabditis elegans has a phosphoproteome atypical for metazoans that is enriched in developmental and sex determination proteins.
Gnad, F; Jedrusik-Bode, M; Mann, M; Wiśniewski, JR; Zielinska, DF, 2009
)
0.35
" However, their use is restricted by such factors as tolerance and opioid-induced hyperalgesia (OIH), so it is critical to find ways to reduce the dosage of opioids to avoid the side effects."( A20 enhances mu-opioid receptor function by inhibiting beta-arrestin2 recruitment.
Li, Y; Shao, S; Su, R; Sun, Y; Tan, B; Tian, X; Zhang, Y, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
serine derivativeAn amino acid derivative resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of serine by a heteroatom. The definition normally excludes peptides containing serine residues.
O-phosphoamino acid
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (6)

PathwayProteinsCompounds
Cysteine Biosynthesis1329
Serine Biosynthesis and Metabolism1020
Secondary Metabolites: Cysteine Biosynthesis from Serine720
Glycine Metabolism1127
Serine Metabolism1025
Neuroinflammation and glutamatergic signaling122

Research

Studies (3,307)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990392 (11.85)18.7374
1990's786 (23.77)18.2507
2000's1201 (36.32)29.6817
2010's778 (23.53)24.3611
2020's150 (4.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.92

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.92 (24.57)
Research Supply Index8.11 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index73.91 (26.88)
Search Engine Supply Index2.02 (0.95)

This Compound (43.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.09%)5.53%
Reviews67 (2.01%)6.00%
Case Studies1 (0.03%)4.05%
Observational0 (0.00%)0.25%
Other3,266 (97.87%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]