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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
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
The steroidogenic acute regulatory protein (StAR): a window into the complexities of intracellular cholesterol trafficking.
1999
Novel neural modulators.
2003
Preferred stereoselective brain uptake of d-serine--a modulator of glutamatergic neurotransmission.
2005 Nov
DOCA-induced phosphorylation of glycogen synthase kinase 3beta.
2006
The presence of high concentrations of free D-amino acids in human saliva.
2006 Mar 6
EAAT1 and D-serine expression are early features of human retinal development.
2007 May
[Interaction between gabapentin and D-serin in the formalin orofacial test].
2009 Dec
Crystallization and preliminary X-ray analysis of a D-Ala:D-Ser ligase associated with VanG-type vancomycin resistance.
2009 Oct 1
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 Jun
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 Fri Dec 15 16:12:06 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:06 GMT 2023
Record UNII
1K77H2Z9B1
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
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