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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
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
Resistance to D-cycloserine in the tubercle bacilli: mutation rate and transport of alanine in parental cells and drug-resistant mutants.
1971 May
Parathyroid hormone-induced lipolysis in human adipose tissue.
1987 May
Localization of plasminogen activator inhibitor type 2 (PAI-2) in hair and nail: implications for terminal differentiation.
1998 Jun
Biochemical activities of minute virus of mice nonstructural protein NS1 are modulated In vitro by the phosphorylation state of the polypeptide.
1998 Oct
Regulation of trespin expression by modulators of cell growth, differentiation, and apoptosis in prostatic epithelial cells.
2003 Apr 1
RBMY, a male germ cell-specific RNA-binding protein, activated in human liver cancers and transforms rodent fibroblasts.
2004 Jul 29
Rap1GAP2 is a new GTPase-activating protein of Rap1 expressed in human platelets.
2005 Apr 15
Autocrine action of adiponectin on human fat cells prevents the release of insulin resistance-inducing factors.
2005 Jul
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).
Name Type Language
SERINE, D-
Systematic Name English
(R)-SERINE
Systematic Name English
SERINE D-FORM [MI]
Common 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 Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
NCI_THESAURUS C29596
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
LOINC 79596-3
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
LOINC 79610-2
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
206-229-4
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
PRIMARY
NSC
77689
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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DRUG BANK
DB03929
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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RXCUI
1742747
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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CHEBI
16523
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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CAS
312-84-5
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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PUBCHEM
71077
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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FDA UNII
1K77H2Z9B1
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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CHEBI
35247
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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NCI_THESAURUS
C61739
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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MERCK INDEX
m9869
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID9041021
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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DAILYMED
1K77H2Z9B1
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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WIKIPEDIA
D-Serine
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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CHEBI
29998
Created by admin on Fri Dec 15 16:12:06 GMT 2023 , Edited by admin on Fri Dec 15 16:12:06 GMT 2023
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