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Product No: AA3243

L-Serine, Extrapure CHR

Name: L-Serine
Brand: Chempure
Rating: 4 (1 reviews)

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CAS Number

56-45-1

Molecular Weight

105.09

Formula

HOCH2CH(NH2)CO2H

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About this item

IUPAC name	(2S)-2-amino-3-hydroxypropanoic acid
canonical smiles	C(C(C(=O)O)N)O
inchi	InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
inchi key	MTCFGRXMJLQNBG-REOHCLBHSA-N
molecular formula	C3H7NO3
synonyms	L-serine serine 56-45-1 (S)-2-Amino-3-hydroxypropanoic acid H-Ser-OH
Compound Description	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. A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines; pyrimidines; and other amino acids. L-Serine is a metabolite found in or produced by Escherichia coli . Serine is a natural product found in Angelica gigas, Pinus densiflora, and other organisms with data available. Serine is a non-essential amino acid in humans , Serine is present and functionally important in many proteins. With an alcohol group, serine is needed for the metabolism of fats, fatty acids, and cell membranes; muscle growth; and a healthy immune system. It also plays a major role in pyrimidine, purine, creatine, and porphyrin biosynthetic pathways. Serine is also found at the active site of the serine protease enzyme class that includes trypsin and chymotrypsin. Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase . Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase . In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, 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. . A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids. See also: Amlisimod .

Computed Properties

Molecular Weight:	105.09 g/mol
XLogP3:	-3.1
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	4
Rotatable Bond Count:	2
Exact Mass:	105.042593085 g/mol
Monoisotopic Mass:	105.042593085 g/mol
Topological Polar Surface Area:	83.6 Å²
Heavy Atom Count:	7
Formal Charge:	0
Complexity:	72.6
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	1
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

Related Compounds

Cysteine

Lactic Acid

Threonine

Serine

Alanine

Proline

(2R)-2-ammonio-3-mercaptopropanoate

Lactic Acid, L-

Penicillamine

Methionine

Valine

Hydroxyproline

4-Hydroxybutanoic acid

D-serine

D-alanine

hazard signal
hazard classes and categories	Not Classified
hazard statements	Not Classified Reported as not meeting GHS hazard criteria by 217 of 232 companies (only ~ 6.5% companies provided GHS information). For more detailed information, please visit ECHA C&L website. Not Classified Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.
hazards summary	Does not appear to reach the fetus of pregnant pigs (placenta metabolizes to glycine). Small increase in resorptions observed in rats following intraperitoneal treatment.

toxicity summary	L-Serine plays a role in cell growth and development . 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.
symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

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About this item

Documentation

Certificate of Analysis

Lot Number

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CAS #

*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!

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About this item

IUPAC name	(2S)-2-amino-3-hydroxypropanoic acid
canonical smiles	C(C(C(=O)O)N)O
inchi	InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
inchi key	MTCFGRXMJLQNBG-REOHCLBHSA-N
molecular formula	C3H7NO3
synonyms	L-serine serine 56-45-1 (S)-2-Amino-3-hydroxypropanoic acid H-Ser-OH
Compound Description	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. A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from glycine or threonine. It is involved in the biosynthesis of purines; pyrimidines; and other amino acids. L-Serine is a metabolite found in or produced by Escherichia coli . Serine is a natural product found in Angelica gigas, Pinus densiflora, and other organisms with data available. Serine is a non-essential amino acid in humans , Serine is present and functionally important in many proteins. With an alcohol group, serine is needed for the metabolism of fats, fatty acids, and cell membranes; muscle growth; and a healthy immune system. It also plays a major role in pyrimidine, purine, creatine, and porphyrin biosynthetic pathways. Serine is also found at the active site of the serine protease enzyme class that includes trypsin and chymotrypsin. Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase . Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase . In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, 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. . A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids. See also: Amlisimod .

Computed Properties

Molecular Weight:	105.09 g/mol
XLogP3:	-3.1
Hydrogen Bond Donor Count:	3
Hydrogen Bond Acceptor Count:	4
Rotatable Bond Count:	2
Exact Mass:	105.042593085 g/mol
Monoisotopic Mass:	105.042593085 g/mol
Topological Polar Surface Area:	83.6 Å²
Heavy Atom Count:	7
Formal Charge:	0
Complexity:	72.6
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	1
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

Related Compounds

Cysteine

Lactic Acid

Threonine

Serine

Alanine

Proline

(2R)-2-ammonio-3-mercaptopropanoate

Lactic Acid, L-

Penicillamine

Methionine

Valine

Hydroxyproline

4-Hydroxybutanoic acid

D-serine

D-alanine

hazard signal
hazard classes and categories	Not Classified
hazard statements	Not Classified Reported as not meeting GHS hazard criteria by 217 of 232 companies (only ~ 6.5% companies provided GHS information). For more detailed information, please visit ECHA C&L website. Not Classified Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.
hazards summary	Does not appear to reach the fetus of pregnant pigs (placenta metabolizes to glycine). Small increase in resorptions observed in rats following intraperitoneal treatment.

toxicity summary	L-Serine plays a role in cell growth and development . 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.
symptoms
carcinogen classification	default_key: No indication of carcinogenicity to humans .

Product No: AA3243

L-Serine, Extrapure CHR

Product No: AA3243

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

Related Compounds

SAFETY AND HAZARDS

TOXICITY

About this item

Documentation

Certificate of Analysis

Require a Sample Certificate of Analysis (COA) ?

Reviews

Product No: AA3243

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

Related Compounds

SAFETY AND HAZARDS

TOXICITY

Require a Sample Certificate of Analysis (COA) ?