SERINE

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 Search

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine palmitoyltransferase 1 2 Target ID: CHEMBL1250343 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22045570	Substrate 661
Serine hydroxymethyltransferase, cytosolic 1 Target ID: CHEMBL1772927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12534373	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Burns 17 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=016822	Primary	Approved 8429	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
Hereditary sensory and autonomic neuropathy type 1 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22045570	Primary	Phase II 1132	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27589995	Primary	Phase II 1132	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://clinicaltrials.gov/ct2/show/NCT03062449	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Towards the molecular basis of sperm and egg interaction during mammalian fertilization.	2001	11114585
cDNA expression cloning and characterization of phosphorylation dependent protein interactors using the yeast tribrid system.	2001	11100482
Identification of receptor tyrosine kinase associating proteins using the yeast two-hybrid system.	2001	11100481
Differential regulation of the uridine nucleotide-activated P2Y4 and P2Y6 receptors. SER-333 and SER-334 in the carboxyl terminus are involved in agonist-dependent phosphorylation desensitization and internalization of the P2Y4 receptor.	2001 Apr 13	11114308
alpha 1-Proteinase inhibitor, alpha 1-antichymotrypsin, and alpha 2-macroglobulin are the antiapoptotic factors of vascular smooth muscle cells.	2001 Apr 13	11096092
Nucleocytoplasmic shuttling of heterodimeric splicing factor U2AF.	2001 Apr 20	11118443
Model systems to assess the destructive potential of human neutrophils and monocyte-derived macrophages during the acute and chronic phases of inflammation.	2001 Feb	11093178
Alterations in the chain dynamics of insoluble elastin upon proteolysis by serine elastases.	2001 Feb	11093116
Phosphorylation-induced change of the oligomerization state of alpha B-crystallin.	2001 Feb 16	11096101
The plant isoflavenoid genistein activates p53 and Chk2 in an ATM-dependent manner.	2001 Feb 16	11096068
Phosphatidylinositol 4-phosphate 5-kinase type I is regulated through phosphorylation response by extracellular stimuli.	2001 Feb 16	11087761
First isolation of human UDP-D-xylose: proteoglycan core protein beta-D-xylosyltransferase secreted from cultured JAR choriocarcinoma cells.	2001 Feb 16	11087729
Heterologous activation of protein kinase C stimulates phosphorylation of delta-opioid receptor at serine 344, resulting in beta-arrestin- and clathrin-mediated receptor internalization.	2001 Feb 16	11085981
Phosphorylation of the pro-apoptotic protein BIK: mapping of phosphorylation sites and effect on apoptosis.	2001 Feb 16	11084041
Myosin I phosphorylation is increased by chemotactic stimulation.	2001 Feb 16	11084033
Elimination of phosphorylation sites of Semliki Forest virus replicase protein nsP3.	2001 Feb 23	11104756
Interaction of paxillin with p21-activated Kinase (PAK). Association of paxillin alpha with the kinase-inactive and the Cdc42-activated forms of PAK3.	2001 Feb 23	11096073
Probing the mechanism of inactivation of human pyruvate dehydrogenase by phosphorylation of three sites.	2001 Feb 23	11092882
The protease inhibitor, MG132, blocks maturation of the amyloid precursor protein Swedish mutant preventing cleavage by beta-Secretase.	2001 Feb 9	11084038
alpha-synuclein is phosphorylated by members of the Src family of protein-tyrosine kinases.	2001 Feb 9	11078745
Chloroplast RNA editing required for functional acetyl-CoA carboxylase in plants.	2001 Feb 9	11078738
Caveolin-1 binding to endoplasmic reticulum membranes and entry into the regulated secretory pathway are regulated by serine phosphorylation. Protein sorting at the level of the endoplasmic reticulum.	2001 Feb 9	11078729
Increasing the thermal stability of euphauserase. A cold-active and multifunctional serine protease from Antarctic krill.	2001 Jan	11121112
Association of alpha(1)-antichymotrypsin deficiency with milder lung disease in patients with cystic fibrosis.	2001 Jan	11120905
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	11118482
In vitro degradation of the Neb-Trypsin modulating oostatic factor (Neb-TMOF) in gut luminal content and hemolymph of the grey fleshfly, Neobellieria bullata.	2001 Jan	11102838
Metabolism of glucagon by dipeptidyl peptidase IV (CD26).	2001 Jan 12	11111019
Characterization of the stromal protease(s) degrading the cross-linked products of the D1 protein generated by photoinhibition of photosystem II.	2001 Jan 19	11115650
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	11114476
Folding pathway mediated by an intramolecular chaperone: the structural and functional characterization of the aqualysin I propeptide.	2001 Jan 5	11114254
Identification of the E2A gene products as regulatory targets of the G1 cyclin-dependent kinases.	2001 Mar 16	11114297
Structure and expression of the murine phosphatidylserine synthase-1 gene.	2001 Mar 16	11084049
Porphyromonas gingivalis DPP-7 represents a novel type of dipeptidylpeptidase.	2001 Mar 2	11096098
Residue Met(156) contributes to the labile enzyme conformation of coagulation factor VIIa.	2001 Mar 2	11078728
Binding of levosimendan, a calcium sensitizer, to cardiac troponin C.	2001 Mar 23	11113122
Polymerization of plasminogen activator inhibitor-1.	2001 Mar 23	11102455
Mutational and X-ray crystallographic analysis of the interaction of dihomo-gamma -linolenic acid with prostaglandin endoperoxide H synthases.	2001 Mar 30	11121413
Cholesterol depletion disrupts caveolae and insulin receptor signaling for metabolic control via insulin receptor substrate-1, but not for mitogen-activated protein kinase control.	2001 Mar 30	11121405
Phosphorylation of tau is regulated by PKN.	2001 Mar 30	11104762
The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase.	2001 Mar 9	11118429
Granzyme B induces BID-mediated cytochrome c release and mitochondrial permeability transition.	2001 Mar 9	11114298
Characterization of phosphatidylserine transport to the locus of phosphatidylserine decarboxylase 2 in permeabilized yeast.	2001 Mar 9	11104779
Substitution of a glycogen synthase kinase-3beta phosphorylation site in presenilin 1 separates presenilin function from beta-catenin signaling.	2001 Mar 9	11104755
Calpain mutants with increased Ca2+ sensitivity and implications for the role of the C(2)-like domain.	2001 Mar 9	11102442
Thermal denaturation of the Na,K-ATPase provides evidence for alpha-alpha oligomeric interaction and gamma subunit association with the C-terminal domain.	2001 Mar 9	11099502
Overexpression and characterization of carboxyl-terminal processing protease for precursor D1 protein: regulation of enzyme-substrate interaction by molecular environments.	2001 Mar 9	11099501
The fission yeast TOR homolog, tor1+, is required for the response to starvation and other stresses via a conserved serine.	2001 Mar 9	11096119
The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa.	2001 Mar 9	11085996
The two major plant plasma membrane H+-ATPases display different regulatory properties.	2001 Mar 9	11080498
The ddcA gene from Streptomyces fradiae encodes an extracellular beta-lactamase with penicillinase and cephalosporinase activities.	2001 Nov 30	11090684

Patents

Sample Use Guides

In Vivo Use Guide

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

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

Name

Type

Language

SERINE

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

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