Basic information
- Standard SMILES
N[C@@H](CO)C(=O)O- InChIKey
MTCFGRXMJLQNBG-REOHCLBHSA-N- Molecular formula
- C3H7NO3
- Average molar mass
- 105.09 g/mol
- Monoisotopic mass
- 105.04259308
Overview
L-serine is the L-enantiomer of serine. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and an algal metabolite. It is a L-alpha-amino acid, a serine, a serine family amino acid and a proteinogenic amino acid. It is a conjugate base of a L-serinium. It is a conjugate acid of a L-serinate. It is an enantiomer of a D-serine. It is a tautomer of a L-serine zwitterion.
Names & identifiers
- Preferred name
- L-Serine
- IUPAC
- (2S)-2-amino-3-hydroxypropanoic acid
- English name
- (2S)-2-amino-3-hydroxy-propanoic acid
- Molecular formula
- C3H7NO3
- Molecular weight
- 0
Names & synonyms
Show more names
Database identifiers
- CAS
302-84-1、56-45-1、6898-95-9- PubChem CID
- 5951
- DTXSID
DTXSID301031857- ChEMBL
CHEMBL11298- ChEBI
CHEBI:17115- UNII
- 452VLY9402
- EC Number
- 200-274-3、630-352-6
- Nikkaji
- J1.195I
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 83.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 72.6
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Serine) -> CIR (Cosmetic Ingredient Review)
Hair conditioning; Antistatic; Skin conditioning
LogP
LogP = -3.07
-3.07
Taste
SWEETISH TASTE, INSIPID AFTERTASTE
Sweet
Color/Form
HEXAGONAL PLATES OR PRISMS
COLORLESS CRYSTALS
Solubility
SOL IN WATER; PRACTICALLY INSOL IN ABSOLUTE ALCOHOL, ETHER
INSOL IN BENZENE, ETHER, ETHANOL
Water solubility = 425 g/L at 25 °C
425.0 mg/mL
Melting Point
228 °C (decomposes)
228 °C
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 94% (236 of 251) of all reports.
Not Classified
Aggregated GHS information provided per 251 reports by companies from 6 notifications to the ECHA C&L Inventory.
Not Classified
Hazard information
Regulatory Information
Chemical: L-Serine
Status: Active Update: 07-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5558
Serine: Does not have an individual approval but may be used under an appropriate group standard
L-serine: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Hazard Classes and Categories
Not Classified
Not Classified
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions
INTRACEREBROVENTRICULAR INJECTIONS OF ALANINE (0.5-2.0 UG) INTO RABBITS CAUSED DECR IN BODY TEMP IN A 10-DEG ENVIRONMENT. THE EFFECT WAS SLIGHTLY SUBADDITIVE WITH THAT OF SERINE.
ERYTHROBLASTIC LEUKEMIC CELLS INCUBATED IN MEDIA CONTAINING ESSENTIAL AMINO ACID L-SERINE BOUND APPROX 30% MORE INSULIN LABELED WITH (125)IODINE THAN THOSE INCUBATED WITHOUT SERINE.
Toxicity Summary
Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.
Human Toxicity Excerpts
HUMAN NEUROBLASTOMA SK-N-SH-SY5Y (5Y) CELLS WERE CULTURED WITH SUPPLEMENTAL SERINE FOR 3-6 DAYS. SERINE HYDROXYMETHYLTRANSFERASE WAS ASSAYED. NO CHANGES IN SPECIFIC ACTIVITY OR CELLULAR MORPHOLOGY WERE NOTED @ CONCN LESS THAN 16 UMOL.
METABOLIC EFFECTS OF CONTROLLED MODIFIED INTAKES OF L-SERINE IN PARENTERAL NUTRITION SOLUTIONS WERE INVESTIGATED IN NORMAL ADULTS.
Non-Human Toxicity Excerpts
ADMIN TO RATS ON DAYS 8-14 OF PREGNANCY, VARIOUS AMINO ACIDS INCL SERINE INCR % RESORPTIONS FROM CONTROL VALUE OF 1.85% TO 5.36-8.85%. ADMIN IP AT 0.1 ML 0.3 MOLAR SOLN/DAY.
RAT GLIOMA CELLS (C6) CULTURED WITH SUPPLEMENTAL SERINE FOR 3-6 DAYS. SERINE HYDROXYMETHYLTRANSFERASE WAS ASSAYED. NO CHANGES IN SPECIFIC ACTIVITY OR CELLULAR MORPHOLOGY NOTED @ CONCN LESS THAN 16 UMOL. CONCN OF 20 AND 40 UMOL LED TO LOWER GLIOMAL ENZYME SPECIFIC ACTIVITIES.
THE GROWTH OF RABBIT HAIR WAS STIMULATED BY L-SERINE.
SERINE INCREASED ETHANOL CONSUMPTION IN ISOLATED HEPATOCYTES FROM 18-HR STARVED AND FED RATS.
Regulatory information
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Chemistry & industry
Pharmacology
Bionecessity
AMINO ACID CLASSED AS NONESSENTIAL FOR MAINTENANCE OF GROWTH IN RATS.
SERINE WAS ESSENTIAL FOR OPTIMAL GROWTH OF EMBRYONIC RAT CELLS IN TISSUE CULTURE. SERINE CAN BE REPLACED BY GLYOXYLIC ACID BUT NOT BY GLYCINE OR GLYCOLIC ACID.
Pharmacodynamics
Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.
Mechanism of Action
L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.
Absorption, Distribution and Excretion
IN PT AGE 2-9 YR, SERINE PRESENT IN ACID MUCOPOLYSACCHARIDES. EXCESSIVE ACCUMULATION & EXCRETION IN URINE OF MUCOPOLYSACCHARIDES MAY BE RELATED TO ABNORMAL BONDING BETWEEN MUCOPOLYSACCHARIDES & PROTEIN.
IN PT AGE 2-9 YR, URINARY SERINE EXCRETION INCR FROM 0.059-0.162 UMOL/24 HR & PLASMA SERINE LEVELS INCR FROM 0.102-0.158 UMOL/ML.
IN PT AGE 2-9 YR, SERINE IS PROBABLY NOT ESTERIFIED THROUGH ITS BETA-HYDROXYL GROUP TO ACID MUCOPOLYSACCHARIDES BUT IS LINKED BY CARBOXYL GROUP.
DETERMINATION OF SERINE LEVELS IN 13 REGIONS OF THE RAT CEREBRAL CORTEX FAILED TO SHOW ANY MARKED DIFFERENCES IN THE AMINO ACID CONTENTS OF CORTEX AREAS OF DIVERSE FUNCTIONS.
Uses & manufacturing
Uses
CIR ingredient: Serine
Non-essential amino acid; [Merck Index] Used in parenteral nutrition, biomedical research, culture media, microbiological tests, feed additives, and skin care creams; [HSDB] Used as a flavoring agent and nutritional supplement for foods; [FDA]
Farming (Feed Additives) [Category: Industry]
Medical use: parenteral nutrition, dietary supplement
IN BIOCHEMICAL RESEARCH, CULTURE MEDIA, MICROBIOLOGICAL TESTS; FEED ADDITIVE; DIETARY SUPPLEMENT
Cosmetics: serine is one component of skin care cream or lotions
Methods of Manufacturing
ISOLATED FROM SILK FIBROIN (SERICINE)
Production methods for L-serine include extraction and fermentation; extraction of hydrolysates and fermentation of glycine substrate are the preferred methods for producing L-serine... microorganisms suggested for the fermentation production of L-serine from glycine include mutants of the genera Pseudomonas, Corynebacterium glycinophilum, and Norcardia
Hydrolysis of protein (especially silk protein); synthesized from glycine
General Manufacturing Information
L-Serine: ACTIVE
Serine: ACTIVE
AMINO ACID COMPOSITION OF SELECTED PROTEINS. SERINE: GELATINS 3.8 G/100 G PROTEIN; MIXED PROTEINS 4.3 G/LB G TOTAL NITROGEN; CASEIN 6.3 G/100 G PROTEIN; SERUM ALBUMIN 7.0 G/100 G PROTEIN; GAMMA-GLOBULIN 11.4 G/100 G PROTEIN; HEMOGLOBIN: HORSE 5.8 G/100 G PROTEIN; INSULIN 5.2 G/100 G PROTEIN; CLOSTRIDIUM BOTULINUM TOXIN 4.4 G/100 G PROTEIN /FROM TABLE/
L- AND D-SERINE EXHIBIT SIMILAR SWEET TASTE QUALITIES.
L-serine can be chemically produced by reacting glycine with formaldehyde
Suppliers3 total
Additional notes
DefinitionChEBI: L-serine is the L-enantiomer of serine. It has a role as a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a serine family amino acid, a proteinogenic amino acid, a L-alpha-amino acid and a serine. It is a conjugate base of a L-serinium. It is a conjugate acid of a L-serinate. It is an enantiomer of a D-serine. It is a tautomer of a L-serine zwitterion.
Related reactions
Linked notes
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