DEXFOSFOSERINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C3H8NO6P
Molecular Weight	185.0725
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](COP(O)(O)=O)C(O)=O

InChI

InChIKey=BZQFBWGGLXLEPQ-REOHCLBHSA-N

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-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17884634 | https://www.ncbi.nlm.nih.gov/pubmed/19747453

Dexfosfoserine (Phosphoserine, L-Serine-O-Phosphate, O-Phosphoserine), the most abundant phosphoamino acid in the eukaryotic phosphoproteome, is not encoded in the genetic code but synthesized posttranslationally. Dexfosfoserine is an agonist of the group III metabotropic glutamate receptors. This endogenous compound inhibits neural stem cells proliferation and promotes survival of nascent neurons thus it has potential therapeutic value in addition to its basic utility as a probe for dissecting molecular mechanisms underlying neurogenesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 4 5 Target ID: Q14833 Gene ID: 2914.0 Gene Symbol: GRM4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9475370	Agonist 2678
Metabotropic glutamate receptor 7 1 Target ID: Q14831 Gene ID: 2917.0 Gene Symbol: GRM7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9475370	Agonist 2678
Metabotropic glutamate receptor 6 6 Target ID: O15303 Gene ID: 2916.0 Gene Symbol: GRM6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9475370	Agonist 2678
Metabotropic glutamate receptor 8 3 Target ID: O00222\|\|\|Q52M02 Gene ID: 2918.0 Gene Symbol: GRM8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9475370	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Theoretical models of catalytic domains of protein phosphatases 1 and 2A with Zn2+ and Mn2+ metal dications and putative bioligands in their catalytic centers.	2001	11440182
Preparation and application of antibodies to phosphoamino acid sequences.	2001	11376433
Ser133 phosphate-KIX interactions in the CREB-CBP complex: an ab initio molecular dynamics study.	2001	11372536
Molecular biology of the plastidic phosphorylated serine biosynthetic pathway in Arabidopsis thaliana.	2001	11354602
Suppressive role of endogenous regucalcin in the regulation of protein phosphatase activity in rat renal cortex cytosol.	2001	11329618
Osmotic stress-dependent serine phosphorylation of the histidine kinase homologue DokA.	2001	11299049
Structural and functional hot spots in cytokine receptors.	2001 Apr	11345195
Protein kinase C delta regulates neural cell adhesion molecule polysialylation state in the rat brain.	2001 Apr	11299305
BCR gene expression blocks Bcr-Abl induced pathogenicity in a mouse model.	2001 Apr 5	11313935
Lysophosphatidic acid-independent platelet activation by low-density lipoprotein.	2001 Apr 6	11297747
Tyrosine hydroxylase phosphorylation in bovine adrenal chromaffin cells: the role of MAPKs after angiotensin II stimulation.	2001 Aug	11483651
Detection of calmodulin-binding proteins and calmodulin-dependent phosphorylation linked to calmodulin-dependent chemotaxis to folic and cAMP in Dictyostelium.	2001 Aug	11483410
Interleukin 2 activates nuclear phospholipase Cbeta by mitogen-activated protein kinase-dependent phosphorylation in human natural killer cells.	2001 Aug	11481231
Insulin stimulates tyrosine phosphorylation and inactivation of protein-tyrosine phosphatase 1B in vivo.	2001 Aug 3	11395511
Zipper-interacting protein kinase induces Ca(2+)-free smooth muscle contraction via myosin light chain phosphorylation.	2001 Aug 3	11384979
Metabotropic glutamate receptors modulate GABA release from mouse hippocampal slices.	2001 Feb	11478745
Association of ErbB2 Ser1113 phosphorylation with epidermal growth factor receptor co-expression and poor prognosis in human breast cancer.	2001 Feb	11330837
Induction of Akt phosphorylation in rat primary astrocytes by H2O2 occurs upstream of phosphatidylinositol 3-kinase: no evidence for oxidative inhibition of PTEN.	2001 Feb 15	11368352
Crystal structure of phosphoserine phosphatase from Methanococcus jannaschii, a hyperthermophile, at 1.8 A resolution.	2001 Jan 10	11342136
MALDI-PSD-MS analysis of the phosphorylation sites of caseinomacropeptide.	2001 Jul	11445239
Structure of GSK3beta reveals a primed phosphorylation mechanism.	2001 Jul	11427888
Phosphorylation of human plasma alpha2-Heremans-Schmid glycoprotein (human fetuin) in vivo.	2001 Jul 15	11439093
Anticonvulsant activity of a mGlu(4alpha) receptor selective agonist, (1S,3R,4S)-1-aminocyclopentane-1,2,4-tricarboxylic acid.	2001 Jul 20	11476756
Phosphorylation of RNA polymerase II CTD fragments results in tight binding to the WW domain from the yeast prolyl isomerase Ess1.	2001 Jul 24	11456485
The length, phosphorylation state, and primary structure of the RNA polymerase II carboxyl-terminal domain dictate interactions with mRNA capping enzymes.	2001 Jul 27	11387325
Structure of the Bacillus cell fate determinant SpoIIAA in phosphorylated and unphosphorylated forms.	2001 Jul 3	11470435
Mitochondrial targeted cytochrome P450 2E1 (P450 MT5) contains an intact N terminus and requires mitochondrial specific electron transfer proteins for activity.	2001 Jul 6	11325963
Ectopic alphaIIbbeta3 integrin signaling involves 12-lipoxygenase- and PKC-mediated serine phosphorylation events in melanoma cells.	2001 Jun	11434681
Helicobacter pylori induces apoptosis in human epithelial gastric cells by stress activated protein kinase pathway.	2001 Jun	11422465
Synergism between nitric oxide and hydrogen peroxide in the inhibition of platelet function: the roles of soluble guanylyl cyclase and vasodilator-stimulated phosphoprotein.	2001 Jun	11384196
Characterization of a novel serine/threonine protein phosphatase (PfPPJ) from the malaria parasite, Plasmodium falciparum.	2001 Jun	11377737
Crystal structure of glycogen synthase kinase 3 beta: structural basis for phosphate-primed substrate specificity and autoinhibition.	2001 Jun 15	11440715
Phosphorylation of plant actin-depolymerising factor by calmodulin-like domain protein kinase.	2001 Jun 15	11418120
Identification of a novel phosphorylation site in human androgen receptor by mass spectrometry.	2001 Jun 15	11396978
Possible implication of the Golgi apparatus casein kinase in the phosphorylation of vesicle docking protein p115 Ser-940: a study with peptide substrates.	2001 Jun 15	11396975
Effects of substitution at serine 40 of tyrosine hydroxylase on catecholamine binding.	2001 Jun 19	11401575
Signal transduction: signaling specificity- a complex affair.	2001 Jun 29	11431552
Modulation of the G protein regulator phosducin by Ca2+/calmodulin-dependent protein kinase II phosphorylation and 14-3-3 protein binding.	2001 Jun 29	11331285
DNA binding of TEA/ATTS domain factors is regulated by protein kinase C phosphorylation in human choriocarcinoma cells.	2001 Jun 29	11313339
Molecular determinants of the interaction between the inositol 1,4,5-trisphosphate receptor-associated cGMP kinase substrate (IRAG) and cGMP kinase Ibeta.	2001 Jun 29	11309393
A p53 amino-terminal nuclear export signal inhibited by DNA damage-induced phosphorylation.	2001 Jun 8	11397945
PhosphoSerine/threonine binding domains: you can't pSERious?	2001 Mar 7	11286893
Phosphopeptides derived from hen egg yolk phosvitin: effect of molecular size on the calcium-binding properties.	2001 May	11440136
Interaction of phosphorylated tyrosine hydroxylase with 14-3-3 proteins: evidence for a phosphoserine 40-dependent association.	2001 May	11359875
Activation of group III mGluRs inhibits GABAergic and glutamatergic transmission in the substantia nigra pars reticulata.	2001 May	11353013
Protein kinase C-mediated desensitization of the neurokinin 1 receptor.	2001 May	11287322
TNF-alpha inhibits flow and insulin signaling leading to NO production in aortic endothelial cells.	2001 May	11287317
The kinase DYRK phosphorylates protein-synthesis initiation factor eIF2Bepsilon at Ser539 and the microtubule-associated protein tau at Thr212: potential role for DYRK as a glycogen synthase kinase 3-priming kinase.	2001 May 1	11311121
Reciprocal phosphorylation and regulation of endothelial nitric-oxide synthase in response to bradykinin stimulation.	2001 May 11	11340086
Mae mediates MAP kinase phosphorylation of Ets transcription factors in Drosophila.	2001 May 17	11357138

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Dexfosfoserine (P-Ser, (10 uM) inhibits neural stem cell/progenitor proliferation and self-renewal, enhances neurogenic fate commitment, and improves neuronal survival.

Name

Type

Language

DEXFOSFOSERINE

Official Name

English

SERIPHOS

Brand Name

English

SERINE, DIHYDROGEN PHOSPHATE (ESTER), L-

Common Name

English

L-SERINE, DIHYDROGEN PHOSPHATE (ESTER)

Systematic Name

English

L-PHOSPHOSERINE

Common Name

English

FOSFORINA

Brand Name

English

L-O-SERINE PHOSPHATE

Common Name

English

SERINE O-PHOSPHATE

Systematic Name

English

L-SERINE, O-PHOSPHONO-

Systematic Name

English

O-PHOSPHOSERINE, L-

Common Name

English

dexfosfoserine [INN]

Common Name

English

GNF-PF-1028

Code

English

PHOSPHOSERINE

Systematic Name

English

PHOSPHOSERINE [MI]

Common Name

English

SERINE PHOSPHATE

Common Name

English

O-PHOSPHORYL-L-SERINE

Common Name

English

L-O-PHOSPHOSERINE

Common Name

English

SERINE PHOSPHATE, L-

Systematic Name

English

(+)-L-SERINE DIHYDROGEN PHOSPHATE (ESTER)

Common Name

English

NSC-760136

Code

English

Dexfosfoserine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73539