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

Molecular Formula	C3H8NO6P
Molecular Weight	185.0725
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.	1999 Apr 20	10216218
Ligand binding to the amino-terminal domain of the mGluR4 subtype of metabotropic glutamate receptor.	1999 Apr 9	10187777
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
Enrichment analysis of phosphorylated proteins as a tool for probing the phosphoproteome.	2001 Apr	11283599
A pyrrolidinone derivative inhibits cytokine-induced iNOS expression and NF-kappaB activation by preventing phosphorylation and degradation of IkappaB-alpha.	2001 Apr	11275558
Cyclin A1 directly interacts with B-myb and cyclin A1/cdk2 phosphorylate B-myb at functionally important serine and threonine residues: tissue-specific regulation of B-myb function.	2001 Apr 1	11264176
Phosphorylation of Ser363, Thr370, and Ser375 residues within the carboxyl tail differentially regulates mu-opioid receptor internalization.	2001 Apr 20	11278523
HIV-1 Tat protein interacts with mammalian capping enzyme and stimulates capping of TAR RNA.	2001 Apr 20	11278368
Dominant negative function by an alternatively spliced form of the interferon-inducible protein kinase PKR.	2001 Apr 27	11278390
Functional replacement of the essential ESS1 in yeast by the plant parvulin DlPar13.	2001 Apr 27	11118437
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
Insulin stimulates tyrosine phosphorylation and inactivation of protein-tyrosine phosphatase 1B in vivo.	2001 Aug 3	11395511
Inhibition of p53-dependent transcription by BOX-I phospho-peptide mimetics that bind to p300.	2001 Feb	11258706
Precise amounts of a novel member of a phosphotransferase superfamily are essential for growth and normal morphology in Caulobacter crescentus.	2001 Feb	11169108
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
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
Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain.	2001 Jan	10913688
A new expression cloning strategy for isolation of substrate-specific kinases by using phosphorylation site-specific antibody.	2001 Jan 1	11150545
Regulation of the ligand binding activity of the human very low density lipoprotein receptor by protein kinase C-dependent phosphorylation.	2001 Jan 5	11010963
Anticonvulsant activity of a mGlu(4alpha) receptor selective agonist, (1S,3R,4S)-1-aminocyclopentane-1,2,4-tricarboxylic acid.	2001 Jul 20	11476756
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
Secretory phospholipase A2 mediates cooperative prostaglandin generation by growth factor and cytokine independently of preceding cytosolic phospholipase A2 expression in rat gastric epithelial cells.	2001 Jun 15	11274144
Signal transduction: signaling specificity- a complex affair.	2001 Jun 29	11431552
Nerve growth factor prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced cell death via the Akt pathway by suppressing caspase-3-like activity using PC12 cells: relevance to therapeutical application for Parkinson's disease.	2001 Mar 1	11223915
Phosphorylation-induced structural changes in the amyloid precursor protein cytoplasmic tail detected by NMR.	2001 Mar 30	11273707
Polyphosphoprotein from the adhesive pads of Mytilus edulis.	2001 Mar 6	11258900
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
14-3-3 Binding to Na+/H+ exchanger isoform-1 is associated with serum-dependent activation of Na+/H+ exchange.	2001 May 11	11279064
Ca2+-independent smooth muscle contraction. a novel function for integrin-linked kinase.	2001 May 11	11278951
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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:28 GMT 2025`
Record UNII	VI4F0K069V
Record Status	`Validated (UNII)`
Record Version

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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