Showing Compound Glycine (FDB000484)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2020-09-17 15:42:09 UTC

Primary ID

FDB000484

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glycine

Description

Glycine, also known as Gly or aminoacetic acid, 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). Glycine is a very strong basic compound (based on its pKa). Glycine exists in all living species, ranging from bacteria to humans. Glycine is an odorless tasting compound. Outside of the human body, Glycine is found, on average, in the highest concentration within a few different foods, such as gelatins, gelatin desserts, and beluga whales and in a lower concentration in hedge mustards, pumpkinseed sunfish, and prunus (cherry, plum). Glycine has also been detected, but not quantified in, several different foods, such as boysenberries, fruit juices, giant butterburs, ginsengs, and Chinese mustards. Glycine is most important and simple, nonessential amino acid in humans, animals, and many mammals. Generally, glycine is synthesized from choline, serine, hydroxyproline, and threonine through interorgan metabolism in which kidneys and liver are the primarily involved. Glycine acts as precursor for several key metabolites of low molecular weight such as creatine, glutathione, haem, purines, and porphyrins. There are a number of reports supporting the role of supplementary glycine in prevention of many diseases and disorders including cancer. Dietary supplementation of glycine is effectual has been shown to be effective in treating metabolic disorders in patients with cardiovascular diseases ( PMID: 25332814), several inflammatory diseases, obesity, cancers, and diabetes ( PMID: 27292783). Glycine has also been shown to enhance the quality of sleep and neurological functions. (PMID: 28337245)

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-222d6c3a1ba6afcd7ea9	2014-09-20	View Spectrum
GC-MS	Glycine, 3 TMS, GC-MS Spectrum	splash10-00dj-2900000000-0ef96bcf06ce475afcdd	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00dj-1900000000-1d289099ac79cfb8bb19	Spectrum
GC-MS	Glycine, 3 TMS, GC-MS Spectrum	splash10-00di-7910000000-6c972a683dfb75b69331	Spectrum
GC-MS	Glycine, 2 TMS, GC-MS Spectrum	splash10-0udi-0900000000-ef69e38ee6cebc2ece00	Spectrum
GC-MS	Glycine, 3 TMS, GC-MS Spectrum	splash10-00di-2910000000-3215b9e40f20c7b306cd	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-719b7f248956f13a312d	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-0udi-0900000000-99b4fc43740b21edc786	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00di-1910000000-4cff4d14c73acff9442f	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00dj-2900000000-0ef96bcf06ce475afcdd	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00dj-1900000000-1d289099ac79cfb8bb19	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-0002-4960000000-2c6fa028e985c6019854	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00di-7910000000-6c972a683dfb75b69331	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00di-2910000000-3215b9e40f20c7b306cd	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-0udi-0900000000-ef69e38ee6cebc2ece00	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-00ds-2900000000-ffffed9c78c16a884e4a	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-004r-3900000000-f288b50b7b6890429811	Spectrum
GC-MS	Glycine, non-derivatized, GC-MS Spectrum	splash10-0udi-1900000000-c76140c31c1f120e4b9d	Spectrum
Predicted GC-MS	Glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9000000000-f0a2cfbefb9fcd9b6c3e	Spectrum
Predicted GC-MS	Glycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9300000000-b8bbfc1276d5adb1ba04	Spectrum
Predicted GC-MS	Glycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-9000000000-725357e461c898a7451e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-9f3930e66b117ad91dca	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-b3336097dddbb5e22871	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-001i-9000000000-719b7f248956f13a312d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-9000000000-6001578fc511ba3fefef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-9000000000-79b2a0a9d93de6a62358	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-9290dbe208c4744f4431	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-9000000000-342ab462db0835abb3d2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0ar1-9010000000-9daadc1d169a8530926d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-07y0-9220000000-8c7785f1f3aa8052679f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0ula-9110000000-43ada06fe1b56b4e9fcc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-017i-9000000000-fbd78fbb48f082235f42	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-004i-9000000000-c38d0fb28793438083a9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Positive	splash10-004i-9000000000-18a7ae48c7b0e15cdf18	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-6001578fc511ba3fefef	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-79b2a0a9d93de6a62358	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-9290dbe208c4744f4431	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-9000000000-605b44ac311a9af4bb7a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-342ab462db0835abb3d2	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0059-9000000000-c6b1ebc1dba89b6a6184	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-851aa6a0263541a8b249	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-d3b5624412082bb2cf60	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-89b2c043a5afe3ebc6f6	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-b4046e208ee8adb87021	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-36521e440c602bd2ca5a	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.5 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

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.