U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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

Description
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

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.

Originator

Sources: Cramer, E. (1865) Ueber die bestandtheile der seide. J. Prakt. Chem. 96, 76–98
Curator's Comment: refernce retrieved from https://www.ncbi.nlm.nih.gov/pubmed/12534373

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FREAMINE III 10%

Approved Use

Parenteral 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 Date

1971
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
2000 Apr 25
cDNA expression cloning and characterization of phosphorylation dependent protein interactors using the yeast tribrid system.
2001
Modulation of 5-HT(1A) receptor activation by its interaction with wild-type and mutant g(alphai3) proteins.
2001
Biochemical characterization of a thrombin-like enzyme and a fibrinolytic serine protease from snake (Agkistrodon saxatilis) venom.
2001 Apr
Purification and characterization of calobin II, a second type of thrombin-like enzyme from Agkistrodon caliginosus (Korean viper).
2001 Apr
Alterations in the chain dynamics of insoluble elastin upon proteolysis by serine elastases.
2001 Feb
Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli.
2001 Feb 16
First isolation of human UDP-D-xylose: proteoglycan core protein beta-D-xylosyltransferase secreted from cultured JAR choriocarcinoma cells.
2001 Feb 16
Phosphorylation of the pro-apoptotic protein BIK: mapping of phosphorylation sites and effect on apoptosis.
2001 Feb 16
The extracellular calcium-sensing receptor dimerizes through multiple types of intermolecular interactions.
2001 Feb 16
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.
2001 Feb 2
Glycogen synthase kinase-3 inhibits the DNA binding activity of NFATc.
2001 Feb 2
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
Ligand-independent dimerization and activation of the oncogenic Xmrk receptor by two mutations in the extracellular domain.
2001 Feb 2
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
Metabolism of glucagon by dipeptidyl peptidase IV (CD26).
2001 Jan 12
Type II transmembrane serine proteases. Insights into an emerging class of cell surface proteolytic enzymes.
2001 Jan 12
Biochemical analysis of the eIF2beta gamma complex reveals a structural function for eIF2alpha in catalyzed nucleotide exchange.
2001 Jan 12
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.
2001 Jan 12
Neuronal nitric-oxide synthase mutant (Ser-1412 --> Asp) demonstrates surprising connections between heme reduction, NO complex formation, and catalysis.
2001 Jan 12
Sites of phosphorylation by protein kinase A in CDC25Mm/GRF1, a guanine nucleotide exchange factor for Ras.
2001 Jan 19
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
Light-induced reorganization of phospholipids in rod disc membranes.
2001 Jan 26
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
Folding pathway mediated by an intramolecular chaperone: the structural and functional characterization of the aqualysin I propeptide.
2001 Jan 5
Functional properties of the active core of human cystathionine beta-synthase crystals.
2001 Jan 5
Regulation of Cbl molecular interactions by the co-receptor molecule CD43 in human T cells.
2001 Jan 5
Lipoarabinomannan from Mycobacterium tuberculosis promotes macrophage survival by phosphorylating Bad through a phosphatidylinositol 3-kinase/Akt pathway.
2001 Jan 5
Structural conservation of neurotropism-associated VspA within the variable Borrelia Vsp-OspC lipoprotein family.
2001 Jan 5
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
Increased expression of protease M in ovarian tumors.
2001 Jan-Feb
Identification of the E2A gene products as regulatory targets of the G1 cyclin-dependent kinases.
2001 Mar 16
Binding of levosimendan, a calcium sensitizer, to cardiac troponin C.
2001 Mar 23
Granzyme B induces BID-mediated cytochrome c release and mitochondrial permeability transition.
2001 Mar 9
Characterization of phosphatidylserine transport to the locus of phosphatidylserine decarboxylase 2 in permeabilized yeast.
2001 Mar 9
Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain.
2001 Mar 9
Overexpression and characterization of carboxyl-terminal processing protease for precursor D1 protein: regulation of enzyme-substrate interaction by molecular environments.
2001 Mar 9
The fission yeast TOR homolog, tor1+, is required for the response to starvation and other stresses via a conserved serine.
2001 Mar 9
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.
2001 Mar 9
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
The ddcA gene from Streptomyces fradiae encodes an extracellular beta-lactamase with penicillinase and cephalosporinase activities.
2001 Nov 30
Patents

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
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 Fri Dec 15 15:15:57 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:57 GMT 2023
Record UNII
452VLY9402
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SERINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
SERINE [USP MONOGRAPH]
Common Name English
Serine (L) [INCI]
Common Name English
SERINE [MART.]
Common Name English
SERINE [HSDB]
Common Name English
serine [INN]
Common Name English
SERINE [EP MONOGRAPH]
Common Name English
SERINE [MI]
Common Name English
L-SERINE
FCC   USP-RS  
Systematic Name English
SERINE [II]
Common Name English
(2S)-2-AMINO-3-HYDROXY-PROPANOIC ACID
Common Name English
L-SERINE [JAN]
Common Name English
SERINE [INCI]
Common Name English
SERINE [VANDF]
Common Name English
SERINE [USAN]
Common Name English
NSC-118365
Code English
L-(-)-SERINE
Common Name English
L-SERINE [USP-RS]
Common Name English
Serine [WHO-DD]
Common Name English
L-SERINE [FCC]
Common Name English
Classification Tree Code System Code
LOINC 2936-3
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LOINC 25523-2
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NCI_THESAURUS C29596
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LOINC 2937-1
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LOINC 17575-2
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DSLD 1687 (Number of products:408)
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LOINC 47743-0
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LOINC 2934-8
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CFR 21 CFR 172.320
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LOINC 26741-9
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DSLD 168 (Number of products:1)
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NCI_THESAURUS C68442
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Code System Code Type Description
MERCK INDEX
m9869
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PRIMARY Merck Index
CHEBI
33384
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PRIMARY
CAS
56-45-1
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PRIMARY
EPA CompTox
DTXSID60883230
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PRIMARY
RS_ITEM_NUM
1612506
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PRIMARY
HSDB
680
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PRIMARY
CHEBI
17115
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PRIMARY
CHEBI
17822
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PRIMARY
EVMPD
SUB10494MIG
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PRIMARY
RXCUI
9671
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PRIMARY RxNorm
ECHA (EC/EINECS)
200-274-3
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PRIMARY
WIKIPEDIA
SERINE
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PRIMARY
DAILYMED
452VLY9402
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PRIMARY
INN
6170
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PRIMARY
PUBCHEM
5951
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PRIMARY
NSC
118365
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PRIMARY
MESH
D012694
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PRIMARY
ChEMBL
CHEMBL11298
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PRIMARY
EVMPD
SUB21990
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PRIMARY
DRUG BANK
DB00133
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PRIMARY
SMS_ID
100000084137
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PRIMARY
DRUG CENTRAL
4127
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PRIMARY
FDA UNII
452VLY9402
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PRIMARY
NCI_THESAURUS
C29613
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PRIMARY
CHEBI
29999
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PRIMARY
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ACTIVE MOIETY