Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (39)transporters (2) Show 41 proteins XML

enzymes (39)transporters (2) Show 41 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2024-05-19 04:25:49 UTC

HMDB ID

HMDB0000123

Secondary Accession Numbers

HMDB00123

Metabolite Identification

Common Name

Glycine

Description

Glycine (Gly), 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. Glycine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glycine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid and is the simplest of all amino acids. In humans, glycine is a nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult human ingests 3 to 5 grams of glycine daily. Glycine is a colorless, sweet-tasting crystalline solid. It is the only achiral proteinogenic amino acid. Glycine was discovered in 1820 by the French chemist Henri Braconnot when he hydrolyzed gelatin by boiling it with sulfuric acid. The name comes from the Greek word glucus or "sweet tasting". Glycine is biosynthesized in the body from the amino acid serine, which is in turn derived from 3-phosphoglycerate. In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). In addition to being synthesized from serine, glycine can also be derived from threonine, choline or hydroxyproline via inter-organ metabolism of the liver and kidneys. Glycine is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine synthase pathway. In this context, the enzyme system involved glycine metabolism is called the glycine cleavage system. The glycine cleavage system catalyzes the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine, and cerebrospinal fluid (CSF) with an increased CSF:plasma glycine ratio (PMID: 16151895 ). Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism (http://www.dcnutrition.com/AminoAcids/). Glycine is elevated by a factor of two or more in the urine of patients with diet-controlled PKU or phenylketonuria (PMID: 37446577 ). Nonketotic hyperglycinaemia (OMIM: 606899 ) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10, and EC 1.8.1.4 for P-, T-, and L-proteins). Mutations have been described in the GLDC (OMIM: 238300 ), AMT (OMIM: 238310 ), and GCSH (OMIM: 238330 ) genes encoding the P-, T-, and H-proteins respectively. Glycine is involved in the body's production of DNA, hemoglobin, and collagen, and in the release of energy. The principal function of glycine is as a precursor to proteins. Most proteins incorporate only small quantities of glycine, a notable exception being collagen, which contains about 35% glycine. In higher eukaryotes, delta-aminolevulinic acid, the key precursor to porphyrins (needed for hemoglobin and cytochromes), is biosynthesized from glycine and succinyl-CoA by the enzyme ALA synthase. Glycine provides the central C2N subunit of all purines, which are key constituents of DNA and RNA. Glycine is an inhibitory neurotransmitter in the central nervous system, especially in the spinal cord, brainstem, and retina. When glycine receptors are activated, chloride enters the neuron via ionotropic receptors, causing an inhibitory postsynaptic potential (IPSP).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aminoacetic acid	ChEBI
Aminoessigsaeure	ChEBI
Aminoethanoic acid	ChEBI
G	ChEBI
Gly	ChEBI
Glycin	ChEBI
Glycocoll	ChEBI
Glykokoll	ChEBI
Glyzin	ChEBI
H2N-CH2-COOH	ChEBI
Hgly	ChEBI
Leimzucker	ChEBI
Aminoacetate	Generator
Aminoethanoate	Generator
2-Aminoacetate	HMDB
2-Aminoacetic acid	HMDB
Aciport	HMDB
Amino-acetate	HMDB
Amino-acetic acid	HMDB
Glicoamin	HMDB
Glycolixir	HMDB
Glycosthene	HMDB
Gyn-hydralin	HMDB
Padil	HMDB
Glycine carbonate (1:1), monosodium salt	HMDB
Glycine carbonate (2:1), monopotassium salt	HMDB
Glycine sulfate (3:1)	HMDB
Glycine, monoammonium salt	HMDB
Glycine, monosodium salt	HMDB
Glycine, sodium hydrogen carbonate	HMDB
Monoammonium salt glycine	HMDB
Calcium salt glycine	HMDB
Glycine hydrochloride (2:1)	HMDB
Glycine phosphate (1:1)	HMDB
Glycine, monopotasssium salt	HMDB
Monopotasssium salt glycine	HMDB
Monosodium salt glycine	HMDB
Glycine carbonate (2:1), monolithium salt	HMDB
Glycine carbonate (2:1), monosodium salt	HMDB
Glycine hydrochloride	HMDB
Glycine, copper salt	HMDB
Hydrochloride, glycine	HMDB
Salt glycine, monoammonium	HMDB
Acid, aminoacetic	HMDB
Cobalt salt glycine	HMDB
Copper salt glycine	HMDB
Glycine phosphate	HMDB
Glycine, calcium salt	HMDB
Glycine, calcium salt (2:1)	HMDB
Glycine, cobalt salt	HMDB
Phosphate, glycine	HMDB
Salt glycine, monosodium	HMDB

Chemical Formula

C₂H₅NO₂

Average Molecular Weight

75.0666

Monoisotopic Molecular Weight

75.032028409

IUPAC Name

2-aminoacetic acid

Traditional Name

glycine

CAS Registry Number

56-40-6

SMILES

NCC(O)=O

InChI Identifier

InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)

InChI Key

DHMQDGOQFOQNFH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Showing metabocard for Glycine (HMDB0000123)

MOL for HMDB0000123 (Glycine)

3D MOL for HMDB0000123 (Glycine)

3D SDF for HMDB0000123 (Glycine)

3D-SDF for HMDB0000123 (Glycine)

PDB for HMDB0000123 (Glycine)

3D PDB for HMDB0000123 (Glycine)

SMILES for HMDB0000123 (Glycine)

INCHI for HMDB0000123 (Glycine)

Structure for HMDB0000123 (Glycine)

3D Structure for HMDB0000123 (Glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra