Human Metabolome Database: Showing metabocard for Serine (HMDB0000187)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19)transporters (1) Show 20 proteins XML

enzymes (19)transporters (1) Show 20 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:54:00 UTC

HMDB ID

HMDB0000187

Secondary Accession Numbers

HMDB0000589
HMDB00187
HMDB00589
HMDB0062263
HMDB62263

Metabolite Identification

Common Name

Serine

Description

Serine (Ser) or L-serine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-serine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Serine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. In humans, serine is a nonessential amino acid that can be easily derived from glycine. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. 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. 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 (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). 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 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. (PMID 12534373 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-hydroxypropanoic acid	ChEBI
(S)-(-)-Serine	ChEBI
(S)-2-Amino-3-hydroxypropanoic acid	ChEBI
(S)-alpha-Amino-beta-hydroxypropionic acid	ChEBI
(S)-Serine	ChEBI
beta-Hydroxy-L-alanine	ChEBI
beta-Hydroxyalanine	ChEBI
L-(-)-Serine	ChEBI
L-2-Amino-3-hydroxypropionic acid	ChEBI
L-3-Hydroxy-2-aminopropionic acid	ChEBI
L-3-Hydroxy-alanine	ChEBI
L-Ser	ChEBI
L-Serin	ChEBI
S	ChEBI
Ser	ChEBI
SERINE	ChEBI
(2S)-2-Amino-3-hydroxypropanoate	Generator
(S)-2-Amino-3-hydroxypropanoate	Generator
(S)-a-Amino-b-hydroxypropionate	Generator
(S)-a-Amino-b-hydroxypropionic acid	Generator
(S)-alpha-Amino-beta-hydroxypropionate	Generator
(S)-Α-amino-β-hydroxypropionate	Generator
(S)-Α-amino-β-hydroxypropionic acid	Generator
b-Hydroxy-L-alanine	Generator
Β-hydroxy-L-alanine	Generator
b-Hydroxyalanine	Generator
Β-hydroxyalanine	Generator
L-2-Amino-3-hydroxypropionate	Generator
L-3-Hydroxy-2-aminopropionate	Generator
(-)-Serine	HMDB
(S)-2-Amino-3-hydroxy-propanoate	HMDB
(S)-2-Amino-3-hydroxy-propanoic acid	HMDB
(S)-b-Amino-3-hydroxypropionate	HMDB
(S)-b-Amino-3-hydroxypropionic acid	HMDB
(S)-beta-Amino-3-hydroxypropionate	HMDB
(S)-beta-Amino-3-hydroxypropionic acid	HMDB
2-Amino-3-hydroxypropanoate	HMDB
2-Amino-3-hydroxypropanoic acid	HMDB
3-Hydroxy-L-alanine	HMDB
L Serine	HMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol	HMDB
Bo-xan	HMDB
e 161b	HMDB
Xanthophyll	HMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol	HMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol	HMDB

Chemical Formula

C₃H₇NO₃

Average Molecular Weight

105.0926

Monoisotopic Molecular Weight

105.042593095

IUPAC Name

(2S)-2-amino-3-hydroxypropanoic acid

Traditional Name

L-serine

CAS Registry Number

56-45-1

SMILES

N[C@@H](CO)C(O)=O

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Serine and derivatives

Alternative Parents