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

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
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
L-amino acid sensing by the extracellular Ca2+-sensing receptor.	2000 Apr 25	10781086
Modulation of 5-HT(1A) receptor activation by its interaction with wild-type and mutant g(alphai3) proteins.	2001	11077069
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
Nucleocytoplasmic shuttling of heterodimeric splicing factor U2AF.	2001 Apr 20	11118443
The plant isoflavenoid genistein activates p53 and Chk2 in an ATM-dependent manner.	2001 Feb 16	11096068
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
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.	2001 Feb 2	11067846
Glycogen synthase kinase-3 inhibits the DNA binding activity of NFATc.	2001 Feb 2	11063740
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	11062248
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
Membrane translocation of novel protein kinase Cs is regulated by phosphorylation of the C2 domain.	2001 Feb 9	11073945
Altered processing of fibronectin in mice lacking heparin. a role for heparin-dependent mast cell chymase in fibronectin degradation.	2001 Feb 9	11035040
Lower serum activity of prolyl endopeptidase in anorexia and bulimia nervosa.	2001 Jan	11070331
Glutaredoxin protects cerebellar granule neurons from dopamine-induced apoptosis by activating NF-kappa B via Ref-1.	2001 Jan 12	11035035
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
Light-induced reorganization of phospholipids in rod disc membranes.	2001 Jan 26	11062249
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 distinct signaling pathways leading to the phosphorylation of interferon regulatory factor 3.	2001 Jan 5	11035028
The phosphatidylethanolamine-binding protein is the prototype of a novel family of serine protease inhibitors.	2001 Jan 5	11034991
Acylation of lysine 983 is sufficient for toxin activity of Bordetella pertussis adenylate cyclase. Substitutions of alanine 140 modulate acylation site selectivity of the toxin acyltransferase CyaC.	2001 Jan 5	11031260
Regulation of the ligand binding activity of the human very low density lipoprotein receptor by protein kinase C-dependent phosphorylation.	2001 Jan 5	11010963
Porphyromonas gingivalis DPP-7 represents a novel type of dipeptidylpeptidase.	2001 Mar 2	11096098
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
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
Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure.	2001 Mar 9	11069906
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	11035189

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

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

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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