Showing Compound Glycine (FDB000484)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2019-11-26 02:54:53 UTC

Primary ID

FDB000484

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glycine

Description

Flavouring ingredient; dietary additive, nutrient Glycine (abbreviated as Gly or G) is the organic compound with the formula NH2CH2COOH. With only a hydrogen atom as its side chain, glycine is the smallest of the 20 amino acids commonly found in proteins. Glycine is unique among the proteinogenic amino acids in that it is not chiral. It can fit into hydrophilic or hydrophobic environment due to its single hydrogen atom side chain. It is coded by codons GGU, GGC, GGA and GGG. Most proteins incorporate only small quantities of glycine. A notable exception is collagen, which contains about 35% glycine. Glycine is a colourless, sweet-tasting crystalline solid.; Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) 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. The glycine cleavage system catalyses 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 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). Strychnine is a strong antagonist at ionotropic glycine receptors, whereas bicuculline is a weak one. Glycine is a required co-agonist along with glutamate for NMDA receptors. In contrast to the inhibitory role of glycine in the spinal cord, this behaviour is facilitated at the (NMDA) glutaminergic receptors which are excitatory.[citation needed] The LD50 of glycine is 7930 mg/kg in rats (oral), and it usually causes death by hyperexcitability.; Glycine is an intermediate in the synthesis of a variety of chemical products. It is used in the manufacture of the herbicide Glyphosate. Glyphosate (N-(phosphonomethyl) glycine) is a non-selective systemic herbicide used to kill weeds, especially perennials and broadcast or used in the cut-stump treatment as a forestry herbicide. Initially, Glyphosate was sold only by Monsanto under the Monsanto tradename Roundup, but is no longer under patent.; Helps trigger the release of oxygen to the energy requiring cell-making process.

CAS Number

56-40-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
Adenine	biospider
Aminoacetic acid, 9CI	db_source
Amitone	biospider
Athenon	biospider
E640	db_source
FEMA 3287	db_source
Glue sugar	db_source

Predicted Properties

Property	Value	Source
Water Solubility	552 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.4	ChemAxon
logS	0.87	ALOGPS
pKa (Strongest Acidic)	2.31	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	16 m³·mol⁻¹	ChemAxon
Polarizability	6.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C2H5NO2

IUPAC name

2-aminoacetic acid

InChI Identifier

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

InChI Key

DHMQDGOQFOQNFH-UHFFFAOYSA-N

Isomeric SMILES

NCC(O)=O

Average Molecular Weight

75.0666

Monoisotopic Molecular Weight

75.032028409

Classification

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:15428 )
proteinogenic amino acid (CHEBI:15428 )
serine family amino acid (CHEBI:15428 )
Common amino acids (C00037 )
Amino acids (C00037 )

Ontology

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Trace element

Molecular messenger:

Neurotransmitter

Industrial application:

Personal care products

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 32.00%; H 6.71%; N 18.66%; O 42.63%	DFC
Melting Point	Mp 292 (262°)° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	249 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.21	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 9.78 (25°)	DFC
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dj-2900000000-0ef96bcf06ce475afcdd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dj-1900000000-1d289099ac79cfb8bb19	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-7910000000-6c972a683dfb75b69331	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-0900000000-ef69e38ee6cebc2ece00	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-2910000000-3215b9e40f20c7b306cd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-719b7f248956f13a312d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-0900000000-99b4fc43740b21edc786	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1910000000-4cff4d14c73acff9442f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-2900000000-0ef96bcf06ce475afcdd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-1900000000-1d289099ac79cfb8bb19	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-0002-4960000000-2c6fa028e985c6019854	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-7910000000-6c972a683dfb75b69331	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2910000000-3215b9e40f20c7b306cd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0900000000-ef69e38ee6cebc2ece00	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ds-2900000000-ffffed9c78c16a884e4a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004r-3900000000-f288b50b7b6890429811	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1900000000-c76140c31c1f120e4b9d	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-f0a2cfbefb9fcd9b6c3e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-b8bbfc1276d5adb1ba04	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-6001578fc511ba3fefef	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-79b2a0a9d93de6a62358	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-9290dbe208c4744f4431	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-6001578fc511ba3fefef	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-79b2a0a9d93de6a62358	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9290dbe208c4744f4431	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-9000000000-605b44ac311a9af4bb7a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-9000000000-725357e461c898a7451e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-9f3930e66b117ad91dca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-b3336097dddbb5e22871	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-001i-9000000000-719b7f248956f13a312d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-9000000000-342ab462db0835abb3d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0ar1-9010000000-9daadc1d169a8530926d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-07y0-9220000000-8c7785f1f3aa8052679f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0ula-9110000000-43ada06fe1b56b4e9fcc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-017i-9000000000-fbd78fbb48f082235f42	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-004i-9000000000-c38d0fb28793438083a9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Positive	splash10-004i-9000000000-18a7ae48c7b0e15cdf18	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-342ab462db0835abb3d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ar1-9010000000-9daadc1d169a8530926d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-07y0-9220000000-8c7785f1f3aa8052679f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ula-9110000000-43ada06fe1b56b4e9fcc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-017i-9000000000-fbd78fbb48f082235f42	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-89b2c043a5afe3ebc6f6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-b4046e208ee8adb87021	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-222d6c3a1ba6afcd7ea9	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

1062

DrugBank ID

DB00145

HMDB ID

HMDB00123

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1008481

SuperScent ID

Not Available

Wikipedia ID

Glycine

Phenol-Explorer Metabolite ID

1062

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti acid			DUKE
anti aldosteronic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti encephalopathic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gastritic			DUKE
anti prostatitic			DUKE
anti pruritic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti sickling			DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
neuro inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
uricosuric			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	CHEBI
neurotransmitter	25512	An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Glycine N-acyltransferase	GLYAT	Q6IB77
Glycine N-acyltransferase-like protein 1	GLYATL1	Q969I3
Glycine N-acyltransferase-like protein 2	GLYATL2	Q8WU03
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial	GCAT	O75600
Trifunctional purine biosynthetic protein adenosine-3	GART	P22102
Alanine--glyoxylate aminotransferase 2, mitochondrial	AGXT2	Q9BYV1
Glycine amidinotransferase, mitochondrial	GATM	P50440
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Glycine--tRNA ligase	GARS	P41250
Aminomethyltransferase, mitochondrial	AMT	P48728
Glutathione synthetase	GSS	P48637
Serine hydroxymethyltransferase, mitochondrial	SHMT2	P34897
Serine hydroxymethyltransferase, cytosolic	SHMT1	P34896
Glycine dehydrogenase [decarboxylating], mitochondrial	GLDC	P23378
Glycine cleavage system H protein, mitochondrial	GCSH	P23434
Vesicular inhibitory amino acid transporter	SLC32A1	Q9H598
Kynurenine--oxoglutarate transaminase 3	CCBL2	Q6YP21
Serine hydroxymethyltransferase	DKFZp686P09201	Q5HYG8

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Ammonia Recycling	SMP00009	map00910
Bile Acid Biosynthesis	SMP00035	map00120
Carnitine Synthesis	SMP00465	Not Available
Glutathione Metabolism	SMP00015	map00480
Glycine and Serine Metabolism	SMP00004	map00260
Methionine Metabolism	SMP00033	map00270
Porphyrin Metabolism	SMP00024	map00860

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Glycine (FDB000484)

Structure for FDB000484 (Glycine)