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-REOHCLBHSA-N
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12534373Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22045570 | https://www.ncbi.nlm.nih.gov/pubmed/27589995 | https://clinicaltrials.gov/ct2/show/NCT03062449
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12534373
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22045570 | https://www.ncbi.nlm.nih.gov/pubmed/27589995 | https://clinicaltrials.gov/ct2/show/NCT03062449
L-serineThe is a non-essential amino acid. L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. L-serine supplementation is in trials for the treatment of several CNS diseases such as Alzheimer's disease, Hereditary sensory and autonomic neuropathy type 1 and Amyotrophic Lateral Sclerosis
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19963421
Curator's Comment: The de novo synthesis of the amino acid L-serine plays an essential role in the development and functioning of the central nervous system (CNS). L-serine displays many metabolic functions during different developmental stages; among its functions providing precursors for amino acids, protein synthesis, nucleotide synthesis, neurotransmitter synthesis and L-serine derived lipids. Patients with congenital defects in the L-serine synthesizing enzymes present with severe neurological abnormalities and underscore the importance of this synthetic pathway.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1250343 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22045570 |
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Target ID: CHEMBL1772927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12534373 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | FREAMINE III 10% Approved UseParenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is
indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric
patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or
should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal
absorption of protein is impaired; or (3) protein requirements are substantially increased as with
extensive burns. Dosage, route of administration, and concomitant infusion of non-protein
calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date1971 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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L-amino acid sensing by the extracellular Ca2+-sensing receptor. | 2000 Apr 25 |
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cDNA expression cloning and characterization of phosphorylation dependent protein interactors using the yeast tribrid system. | 2001 |
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Modulation of 5-HT(1A) receptor activation by its interaction with wild-type and mutant g(alphai3) proteins. | 2001 |
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Biochemical characterization of a thrombin-like enzyme and a fibrinolytic serine protease from snake (Agkistrodon saxatilis) venom. | 2001 Apr |
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Purification and characterization of calobin II, a second type of thrombin-like enzyme from Agkistrodon caliginosus (Korean viper). | 2001 Apr |
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Alterations in the chain dynamics of insoluble elastin upon proteolysis by serine elastases. | 2001 Feb |
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Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli. | 2001 Feb 16 |
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First isolation of human UDP-D-xylose: proteoglycan core protein beta-D-xylosyltransferase secreted from cultured JAR choriocarcinoma cells. | 2001 Feb 16 |
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Phosphorylation of the pro-apoptotic protein BIK: mapping of phosphorylation sites and effect on apoptosis. | 2001 Feb 16 |
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The extracellular calcium-sensing receptor dimerizes through multiple types of intermolecular interactions. | 2001 Feb 16 |
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A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling. | 2001 Feb 2 |
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Glycogen synthase kinase-3 inhibits the DNA binding activity of NFATc. | 2001 Feb 2 |
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Molecular cloning and characterization of the human protein kinase D2. A novel member of the protein kinase D family of serine threonine kinases. | 2001 Feb 2 |
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Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain. | 2001 Feb 2 |
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Utilizing the peptidyl-prolyl cis-trans isomerase pin1 as a probe of its phosphorylated target proteins. Examples of binding to nuclear proteins in a human kidney cell line and to tau in Alzheimer's diseased brain. | 2001 Jan |
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Metabolism of glucagon by dipeptidyl peptidase IV (CD26). | 2001 Jan 12 |
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Type II transmembrane serine proteases. Insights into an emerging class of cell surface proteolytic enzymes. | 2001 Jan 12 |
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Biochemical analysis of the eIF2beta gamma complex reveals a structural function for eIF2alpha in catalyzed nucleotide exchange. | 2001 Jan 12 |
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Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates. | 2001 Jan 12 |
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Neuronal nitric-oxide synthase mutant (Ser-1412 --> Asp) demonstrates surprising connections between heme reduction, NO complex formation, and catalysis. | 2001 Jan 12 |
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Sites of phosphorylation by protein kinase A in CDC25Mm/GRF1, a guanine nucleotide exchange factor for Ras. | 2001 Jan 19 |
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Calmodulin kinase II attenuation of gene transcription by preventing cAMP response element-binding protein (CREB) dimerization and binding of the CREB-binding protein. | 2001 Jan 19 |
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Light-induced reorganization of phospholipids in rod disc membranes. | 2001 Jan 26 |
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Exaggerated responses to chronic nociceptive stimuli and enhancement of N-methyl-D-aspartate receptor-mediated synaptic transmission in mutant mice lacking D-amino-acid oxidase. | 2001 Jan 5 |
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Folding pathway mediated by an intramolecular chaperone: the structural and functional characterization of the aqualysin I propeptide. | 2001 Jan 5 |
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Functional properties of the active core of human cystathionine beta-synthase crystals. | 2001 Jan 5 |
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Regulation of Cbl molecular interactions by the co-receptor molecule CD43 in human T cells. | 2001 Jan 5 |
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Lipoarabinomannan from Mycobacterium tuberculosis promotes macrophage survival by phosphorylating Bad through a phosphatidylinositol 3-kinase/Akt pathway. | 2001 Jan 5 |
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Structural conservation of neurotropism-associated VspA within the variable Borrelia Vsp-OspC lipoprotein family. | 2001 Jan 5 |
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Crystal structure of the CCAAT box/enhancer-binding protein beta activating transcription factor-4 basic leucine zipper heterodimer in the absence of DNA. | 2001 Jan 5 |
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Increased expression of protease M in ovarian tumors. | 2001 Jan-Feb |
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Identification of the E2A gene products as regulatory targets of the G1 cyclin-dependent kinases. | 2001 Mar 16 |
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Binding of levosimendan, a calcium sensitizer, to cardiac troponin C. | 2001 Mar 23 |
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Granzyme B induces BID-mediated cytochrome c release and mitochondrial permeability transition. | 2001 Mar 9 |
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Characterization of phosphatidylserine transport to the locus of phosphatidylserine decarboxylase 2 in permeabilized yeast. | 2001 Mar 9 |
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Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain. | 2001 Mar 9 |
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Overexpression and characterization of carboxyl-terminal processing protease for precursor D1 protein: regulation of enzyme-substrate interaction by molecular environments. | 2001 Mar 9 |
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The fission yeast TOR homolog, tor1+, is required for the response to starvation and other stresses via a conserved serine. | 2001 Mar 9 |
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The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa. | 2001 Mar 9 |
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Deletion of aprA and nprA genes for alkaline protease A and neutral protease A from bacillus thuringiensis: effect on insecticidal crystal proteins. | 2001 Nov 17 |
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The ddcA gene from Streptomyces fradiae encodes an extracellular beta-lactamase with penicillinase and cephalosporinase activities. | 2001 Nov 30 |
Sample Use Guides
Hereditary sensory and autonomic neuropathy type 1 (HSAN1) patients: 10-week oral l-serine 200 or 400 mg/kg body weight.
Amyotrophic Lateral Sclerosis patients: twice-daily dose regimens (0.5, 2.5, 7.5, or 15 g/dose).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22045570
Increasing L-serine medium concentrations (1-10 mM) substantially suppressed endogenous deoxysphinganine production in WT serine palmitoyltransferase SPTLC1 and hereditary sensory and autonomic neuropathy type 1 (HSAN1) mutant–expressing HEK293 cells
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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Record UNII |
452VLY9402
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Record Status |
Validated (UNII)
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Record Version |
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C68442
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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