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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28318835
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2842779
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
Edited
Mon Mar 31 18:21:40 GMT 2025
by
admin
on
Mon Mar 31 18:21:40 GMT 2025
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| Record UNII |
1K77H2Z9B1
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| Record Status |
Validated (UNII)
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| Record Version |
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LOINC |
79648-2
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NCI_THESAURUS |
C29596
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LOINC |
79596-3
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LOINC |
79610-2
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206-229-4
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77689
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DB03929
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1742747
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16523
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312-84-5
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71077
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1K77H2Z9B1
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35247
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C61739
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m9869
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DTXSID9041021
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1K77H2Z9B1
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D-Serine
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29998
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PARENT -> IMPURITY |
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