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

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 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
Binding of [3H](2S,1'S,2'S)-2-(9-xanthylmethyl)-2-(2'-carboxycyclopropyl) glycine ([3H]LY341495) to cell membranes expressing recombinant human group III metabotropic glutamate receptor subtypes.	2000 Dec	11138847
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
Structural and functional hot spots in cytokine receptors.	2001 Apr	11345195
A pyrrolidinone derivative inhibits cytokine-induced iNOS expression and NF-kappaB activation by preventing phosphorylation and degradation of IkappaB-alpha.	2001 Apr	11275558
Dominant negative function by an alternatively spliced form of the interferon-inducible protein kinase PKR.	2001 Apr 27	11278390
Tyrosine hydroxylase phosphorylation in bovine adrenal chromaffin cells: the role of MAPKs after angiotensin II stimulation.	2001 Aug	11483651
Interleukin 2 activates nuclear phospholipase Cbeta by mitogen-activated protein kinase-dependent phosphorylation in human natural killer cells.	2001 Aug	11481231
NF-kappaB-inducing kinase regulates the processing of NF-kappaB2 p100.	2001 Feb	11239468
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
Downregulation of MDM2 stabilizes p53 by inhibiting p53 ubiquitination in response to specific alkylating agents.	2001 Feb 16	11223035
Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli.	2001 Feb 16	11087761
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
Stoichiometric phosphorylation of human p53 at Ser315 stimulates p53-dependent transcription.	2001 Feb 16	11078726
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
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
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
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
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
Effects of substitution at serine 40 of tyrosine hydroxylase on catecholamine binding.	2001 Jun 19	11401575
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
Expression of l-3-phosphoserine phosphatase is regulated by reconstituted basement membrane.	2001 Mar 2	11237721
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
Reciprocal phosphorylation and regulation of endothelial nitric-oxide synthase in response to bradykinin stimulation.	2001 May 11	11340086
14-3-3 Binding to Na+/H+ exchanger isoform-1 is associated with serum-dependent activation of Na+/H+ exchange.	2001 May 11	11279064

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 `Fri Dec 15 16:33:44 UTC 2023` Edited by `admin` on `Fri Dec 15 16:33:44 UTC 2023`
Record UNII	VI4F0K069V
Record Status	`Validated (UNII)`
Record Version

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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