DEXFOSFOSERINE

Investigational

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 2752
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 2752
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 2752
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 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

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
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
On-membrane digestion of beta-casein for determination of phosphorylation sites by matrix-assisted laser desorption/ionization quadrupole/time-of-flight mass spectrometry.	2001	11180550
Protein kinase C delta regulates neural cell adhesion molecule polysialylation state in the rat brain.	2001 Apr	11299305
HIV-1 Tat protein interacts with mammalian capping enzyme and stimulates capping of TAR RNA.	2001 Apr 20	11278368
Cyclic AMP inhibits Akt activity by blocking the membrane localization of PDK1.	2001 Apr 20	11278269
Dominant negative function by an alternatively spliced form of the interferon-inducible protein kinase PKR.	2001 Apr 27	11278390
Functional conservation of phosphorylation-specific prolyl isomerases in plants.	2001 Apr 27	11118438
Functional replacement of the essential ESS1 in yeast by the plant parvulin DlPar13.	2001 Apr 27	11118437
BCR gene expression blocks Bcr-Abl induced pathogenicity in a mouse model.	2001 Apr 5	11313935
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
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
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
Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli.	2001 Feb 16	11087761
3-phosphoinositide-dependent protein kinase 1, an Akt1 kinase, is involved in dephosphorylation of Thr-308 of Akt1 in Chinese hamster ovary cells.	2001 Feb 16	11087733
Heterologous activation of protein kinase C stimulates phosphorylation of delta-opioid receptor at serine 344, resulting in beta-arrestin- and clathrin-mediated receptor internalization.	2001 Feb 16	11085981
Novel properties of the protein kinase CK2-site-regulated nuclear- localization sequence of the interferon-induced nuclear factor IFI 16.	2001 Jan 1	11115400
Crystal structure of phosphoserine phosphatase from Methanococcus jannaschii, a hyperthermophile, at 1.8 A resolution.	2001 Jan 10	11342136
Activation of dopamine D(1)-like receptor causes phosphorylation of alpha(1)-subunit of Na(+),K(+)-ATPase in rat renal proximal tubules.	2001 Jan 5	11137859
MALDI-PSD-MS analysis of the phosphorylation sites of caseinomacropeptide.	2001 Jul	11445239
Elevated levels of group-III metabotropic glutamate receptors in the inferior colliculus of genetically epilepsy-prone rats following intracollicular administration of L-serine-O-phosphate.	2001 Jul	11432969
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
Rsk2 allosterically activates estrogen receptor alpha by docking to the hormone-binding domain.	2001 Jul 2	11432835
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
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
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
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
ASK1-signaling promotes c-Myc protein stability during apoptosis.	2001 Mar	11243879
Polyphosphoprotein from the adhesive pads of Mytilus edulis.	2001 Mar 6	11258900
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
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
ATM-dependent phosphorylation of human Rad9 is required for ionizing radiation-induced checkpoint activation.	2001 May 11	11278446
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

PHOSPHOSERINE

Preferred Name

English

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 [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