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Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7NO3
Molecular Weight 105.0926
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SERINE, D-

SMILES

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

InChI

InChIKey=MTCFGRXMJLQNBG-UWTATZPHSA-N
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1

HIDE SMILES / InChI

Molecular Formula C3H7NO3
Molecular Weight 105.0926
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

SERINE, D- (D-serine) is a non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines, pyrimidines and other amino acids. A considerable level of D-serine was discovered, surprisingly, in the mammalian brain in the early 1990s. Since then, D-serine has been considered to be a co-agonist of glutamate at the glycine site of NMDA receptors. D-serine plays an important role in the central nervous system as an endogenous ligand for the glycine site of glutamate N-Methyl-D-Aspartate (NMDA) receptors. D-serine is synthetized by racemization of L-serine in most neural and non-neural cells, and modulates a variety of physiological functions in mammals. D-Serine synthesis is attributed to Serine Racemase (SR), which catalyses the synthesis of D-serine from L-serine. D-serine may play a role in the pathophysiology of neuropsychiatric disorders, such as schizophrenia, which may be linked to NMDA receptor hypo-function. Studies in genetic and pharmacological animal models with decreased D-serine levels have shown that these animals displayed behavioural abnormalities similar to those seen in schizophrenia. Moreover, exogenous administration of D-serine and related compounds improved several phenotypes relevant to schizophrenia, which could have positive clinical implications in humans. The results of a clinical trial in Taiwanese schizophrenic patients who received D-serine as adjuvant treatment indicated that those patients who received D-serine treatment, improved positive, negative and cognitive symptoms seen in schizophrenia. In addition, this clinical trial showed that D-serine did not worsen side effects from other antipsychotics, which may be due to its selective action at the NMDA-glycine site. Therefore, D-serine could be considered as a therapeutic approach for schizophrenia, which is different from the dopaminergic approach. It has also been shown that exogenous d-serine administration can suppress appetite and alter food preference. Thus NMDA receptor and its co-agonist d-seine participate in the control of appetite and food preference, which can be used to suppress obesity. D-serine has been shown to have cognitive-enhancing properties in different brain disorders and in age-related cognitive decline. From a clinical perspective, it is important to highlight that in a recent double-blind placebo-controlled cross-over study our group observed that an acute oral administration of 30 mg/kg of d-serine improved spatial learning and problem solving. D-serine may be especially useful for depression because of its acute and chronic antidepressant effects,

Approval Year

PubMed

PubMed

TitleDatePubMed
D-Serine metabolism in C6 glioma cells: Involvement of alanine-serine-cysteine transporter (ASCT2) and serine racemase (SRR) but not D-amino acid oxidase (DAO).
2010-06
[Interaction between gabapentin and D-serin in the formalin orofacial test].
2009-12
Crystallization and preliminary X-ray analysis of a D-Ala:D-Ser ligase associated with VanG-type vancomycin resistance.
2009-10-01
EAAT1 and D-serine expression are early features of human retinal development.
2007-05
D1 dopamine receptor hyperphosphorylation in renal proximal tubules in hypertension.
2006-09
Phosphorylation of Jak2 on Ser(523) inhibits Jak2-dependent leptin receptor signaling.
2006-06
Targeting the RNA splicing machinery as a novel treatment strategy for pancreatic carcinoma.
2006-04-01
Signal transducer and activator of transcription 3 is required for the oncogenic effects of non-small-cell lung cancer-associated mutations of the epidermal growth factor receptor.
2006-03-15
The presence of high concentrations of free D-amino acids in human saliva.
2006-03-06
Neurotransmitter transporters and their impact on the development of psychopharmacology.
2006-01
Reference data for cerebrospinal fluid and the utility of amino acid measurement for the diagnosis of inborn errors of metabolism.
2006-01
Biochemical characterization of biocontrol agents used for control of root pathogens.
2006
DOCA-induced phosphorylation of glycogen synthase kinase 3beta.
2006
Reduced mitochondrial density and increased IRS-1 serine phosphorylation in muscle of insulin-resistant offspring of type 2 diabetic parents.
2005-12
Preferred stereoselective brain uptake of d-serine--a modulator of glutamatergic neurotransmission.
2005-11
Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1.
2005-09
Platelet endothelial aggregation receptor 1 (PEAR1), a novel epidermal growth factor repeat-containing transmembrane receptor, participates in platelet contact-induced activation.
2005-07-01
Autocrine action of adiponectin on human fat cells prevents the release of insulin resistance-inducing factors.
2005-07
Rap1GAP2 is a new GTPase-activating protein of Rap1 expressed in human platelets.
2005-04-15
Increased activation of the mammalian target of rapamycin pathway in liver and skeletal muscle of obese rats: possible involvement in obesity-linked insulin resistance.
2005-03
PKC-theta knockout mice are protected from fat-induced insulin resistance.
2004-09
Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide.
2004-08-01
RBMY, a male germ cell-specific RNA-binding protein, activated in human liver cancers and transforms rodent fibroblasts.
2004-07-29
Apoptosis signaling by the novel compound 3-Cl-AHPC involves increased EGFR proteolysis and accompanying decreased phosphatidylinositol 3-kinase and AKT kinase activities.
2004-03-11
GDNF-deprived sympathetic neurons die via a novel nonmitochondrial pathway.
2003-12-08
The vanG glycopeptide resistance operon from Enterococcus faecalis revisited.
2003-11
Distribution and pharmacology of alanine-serine-cysteine transporter 1 (asc-1) in rodent brain.
2003-10
Uropathogenic Escherichia coli use d-serine deaminase to modulate infection of the murine urinary tract.
2003-07
Regulation of trespin expression by modulators of cell growth, differentiation, and apoptosis in prostatic epithelial cells.
2003-04-01
Novel neural modulators.
2003
Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon.
2002-02-22
Expression and characterization of trypsinogen produced in the human male genital tract.
2000-12
Decreased elastin deposition and high proliferation of fibroblasts from Costello syndrome are related to functional deficiency in the 67-kD elastin-binding protein.
2000-03
Testisin, a new human serine proteinase expressed by premeiotic testicular germ cells and lost in testicular germ cell tumors.
1999-07-01
The steroidogenic acute regulatory protein (StAR): a window into the complexities of intracellular cholesterol trafficking.
1999
Biochemical activities of minute virus of mice nonstructural protein NS1 are modulated In vitro by the phosphorylation state of the polypeptide.
1998-10
Localization of plasminogen activator inhibitor type 2 (PAI-2) in hair and nail: implications for terminal differentiation.
1998-06
Spreading and migration of human glioma and rat C6 cells on central nervous system myelin in vitro is correlated with tumor malignancy and involves a metalloproteolytic activity.
1998-01-01
Constitutive and inducible expression of SKALP/elafin provides anti-elastase defense in human epithelia.
1996-09-15
Antileukoprotease inhibits stratum corneum chymotryptic enzyme. Evidence for a regulative function in desquamation.
1996-09-06
Calpain secreted by activated human lymphoid cells degrades myelin.
1995-10-01
The endogenous vascular elastase that governs development and progression of monocrotaline-induced pulmonary hypertension in rats is a novel enzyme related to the serine proteinase adipsin.
1994-09
Cloning, expression, and characterization of stratum corneum chymotryptic enzyme. A skin-specific human serine proteinase.
1994-07-29
Cloning and expression of a novel Na(+)-dependent neutral amino acid transporter structurally related to mammalian Na+/glutamate cotransporters.
1993-07-25
Parathyroid hormone-induced lipolysis in human adipose tissue.
1987-05
Resistance to D-cycloserine in the tubercle bacilli: mutation rate and transport of alanine in parental cells and drug-resistant mutants.
1971-05
Patents

Sample Use Guides

D-serine treatment in schizophrenia: Primary analysis was on MMN after double-blind crossover (60mg/kg/d, n=16, 6weeks) treatment with d-serine/placebo. Secondary measures included clinical symptoms, neurocognition, and the effects of open-label (30-120mg/kg/d, n=21) d-serine and bitopertin/placebo (10mg, n=29), a glycine transport inhibitor. These findings represent the first randomized double-blind placebo-controlled study with 60mg/kg d-serine in schizophrenia, and are consistent with meta-analyses showing significant effects of d-serine in schizophrenia.
Route of Administration: Oral
In Vitro Use Guide
In rat cortical slices 7-Cl KYNA (10-100 uM) noncompetitively inhibited N-Me-D-Asp responses, and this effect could be reversed by the addition of glycine (100 uM) or D-serine (100 uM).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:21:40 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:40 GMT 2025
Record UNII
1K77H2Z9B1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SERINE, D-
Systematic Name English
SERINE D-FORM
MI  
Preferred Name English
(R)-SERINE
Systematic Name English
SERINE D-FORM [MI]
Common Name English
(R)-2-AMINO-3-HYDROXYPROPANOIC ACID
Systematic Name English
D-SERINE
Systematic Name English
NSC-77689
Code English
Classification Tree Code System Code
LOINC 79648-2
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
NCI_THESAURUS C29596
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
LOINC 79596-3
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
LOINC 79610-2
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
206-229-4
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
NSC
77689
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
DRUG BANK
DB03929
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
RXCUI
1742747
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
CHEBI
16523
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
CAS
312-84-5
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
PUBCHEM
71077
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
FDA UNII
1K77H2Z9B1
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
CHEBI
35247
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
NCI_THESAURUS
C61739
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
MERCK INDEX
m9869
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID9041021
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
DAILYMED
1K77H2Z9B1
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
WIKIPEDIA
D-Serine
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
CHEBI
29998
Created by admin on Mon Mar 31 18:21:40 GMT 2025 , Edited by admin on Mon Mar 31 18:21:40 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY