U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DEXFOSFOSERINE

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
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q14833
Gene ID: 2914.0
Gene Symbol: GRM4
Target Organism: Homo sapiens (Human)
Target ID: Q14831
Gene ID: 2917.0
Gene Symbol: GRM7
Target Organism: Homo sapiens (Human)
Target ID: O15303
Gene ID: 2916.0
Gene Symbol: GRM6
Target Organism: Homo sapiens (Human)
Target ID: O00222|||Q52M02
Gene ID: 2918.0
Gene Symbol: GRM8
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Plastidic pathway of serine biosynthesis. Molecular cloning and expression of 3-phosphoserine phosphatase from Arabidopsis thaliana.
1999 Apr 16
Preparation and application of antibodies to phosphoamino acid sequences.
2001
HIV-1 Tat protein interacts with mammalian capping enzyme and stimulates capping of TAR RNA.
2001 Apr 20
Lysophosphatidic acid-independent platelet activation by low-density lipoprotein.
2001 Apr 6
Insulin stimulates tyrosine phosphorylation and inactivation of protein-tyrosine phosphatase 1B in vivo.
2001 Aug 3
Zipper-interacting protein kinase induces Ca(2+)-free smooth muscle contraction via myosin light chain phosphorylation.
2001 Aug 3
Nerve growth factor inhibits PC12 cell PDE 2 phosphodiesterase activity and increases PDE 2 binding to phosphoproteins.
2001 Feb
Kinase suppressor of ras is necessary for tumor necrosis factor alpha activation of extracellular signal-regulated kinase/mitogen-activated protein kinase in intestinal epithelial cells.
2001 Feb 1
Downregulation of MDM2 stabilizes p53 by inhibiting p53 ubiquitination in response to specific alkylating agents.
2001 Feb 16
Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli.
2001 Feb 16
Myosin I phosphorylation is increased by chemotactic stimulation.
2001 Feb 16
Stoichiometric phosphorylation of human p53 at Ser315 stimulates p53-dependent transcription.
2001 Feb 16
Regulation of the ligand binding activity of the human very low density lipoprotein receptor by protein kinase C-dependent phosphorylation.
2001 Jan 5
Phosphorylation of human plasma alpha2-Heremans-Schmid glycoprotein (human fetuin) in vivo.
2001 Jul 15
Phosphorylation of RNA polymerase II CTD fragments results in tight binding to the WW domain from the yeast prolyl isomerase Ess1.
2001 Jul 24
The length, phosphorylation state, and primary structure of the RNA polymerase II carboxyl-terminal domain dictate interactions with mRNA capping enzymes.
2001 Jul 27
Structure of the Bacillus cell fate determinant SpoIIAA in phosphorylated and unphosphorylated forms.
2001 Jul 3
Mitochondrial targeted cytochrome P450 2E1 (P450 MT5) contains an intact N terminus and requires mitochondrial specific electron transfer proteins for activity.
2001 Jul 6
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
Characterization of a novel serine/threonine protein phosphatase (PfPPJ) from the malaria parasite, Plasmodium falciparum.
2001 Jun
Crystal structure of glycogen synthase kinase 3 beta: structural basis for phosphate-primed substrate specificity and autoinhibition.
2001 Jun 15
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
Roles of the forkhead in rhabdomyosarcoma (FKHR) phosphorylation sites in regulating 14-3-3 binding, transactivation and nuclear targetting.
2001 Mar 15
Expression of l-3-phosphoserine phosphatase is regulated by reconstituted basement membrane.
2001 Mar 2
Phosphopeptides derived from hen egg yolk phosvitin: effect of molecular size on the calcium-binding properties.
2001 May
Protein kinase C-mediated desensitization of the neurokinin 1 receptor.
2001 May
Reciprocal phosphorylation and regulation of endothelial nitric-oxide synthase in response to bradykinin stimulation.
2001 May 11
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
INN   WHO-DD  
INN  
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  
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
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
Code System Code Type Description
EVMPD
SUB07029MIG
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
FDA UNII
VI4F0K069V
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID1046348
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL284377
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
CHEBI
45522
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
DRUG CENTRAL
4120
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
NSC
760136
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
INN
6888
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
EVMPD
SUB33464
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-986-0
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
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DRUG BANK
DB04522
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
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MERCK INDEX
m8745
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY Merck Index
SMS_ID
100000083223
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
PUBCHEM
68841
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
NCI_THESAURUS
C169894
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
CHEBI
15811
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
WIKIPEDIA
Phosphoserine
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
CAS
407-41-0
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY
CHEBI
37712
Created by admin on Fri Dec 15 16:33:45 GMT 2023 , Edited by admin on Fri Dec 15 16:33:45 GMT 2023
PRIMARY