Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2018-05-28 23:01:52 UTC
Primary IDFDB000484
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycine
DescriptionFlavouring 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 Number56-40-6
Structure
Thumb
Synonyms
SynonymSource
Aminoacetic acidChEBI
AminoessigsaeureChEBI
Aminoethanoic acidChEBI
GChEBI
GlyChEBI
GlycinChEBI
GlycocollChEBI
GlykokollChEBI
GlyzinChEBI
H2N-CH2-COOHChEBI
HglyChEBI
LeimzuckerChEBI
AminoacetateGenerator
AminoethanoateGenerator
2-AminoacetateHMDB
2-Aminoacetic acidHMDB
AciportHMDB
Amino-acetateHMDB
Amino-acetic acidHMDB
GlicoaminHMDB
GlycolixirHMDB
GlycostheneHMDB
Gyn-hydralinHMDB
PadilHMDB
Glycine carbonate (1:1), monosodium saltHMDB
Glycine carbonate (2:1), monopotassium saltHMDB
Glycine sulfate (3:1)HMDB
Glycine, monoammonium saltHMDB
Glycine, monosodium saltHMDB
Glycine, sodium hydrogen carbonateHMDB
Monoammonium salt glycineHMDB
Calcium salt glycineHMDB
Glycine hydrochloride (2:1)HMDB
Glycine phosphate (1:1)HMDB
Glycine, monopotasssium saltHMDB
Monopotasssium salt glycineHMDB
Monosodium salt glycineHMDB
Glycine carbonate (2:1), monolithium saltHMDB
Glycine carbonate (2:1), monosodium saltHMDB
Glycine hydrochlorideHMDB
Glycine, copper saltHMDB
Hydrochloride, glycineHMDB
Salt glycine, monoammoniumHMDB
Acid, aminoaceticHMDB
Cobalt salt glycineHMDB
Copper salt glycineHMDB
Glycine phosphateHMDB
Glycine, calcium saltHMDB
Glycine, calcium salt (2:1)HMDB
Glycine, cobalt saltHMDB
Phosphate, glycineHMDB
Salt glycine, monosodiumHMDB
Adeninebiospider
Aminoacetic acid, 9CIdb_source
Amitonebiospider
Athenonbiospider
E640db_source
FEMA 3287db_source
Glue sugardb_source
Predicted Properties
PropertyValueSource
Water Solubility552 g/LALOGPS
logP-3.3ALOGPS
logP-3.4ChemAxon
logS0.87ALOGPS
pKa (Strongest Acidic)2.31ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16 m³·mol⁻¹ChemAxon
Polarizability6.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC2H5NO2
IUPAC name2-aminoacetic acid
InChI IdentifierInChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
InChI KeyDHMQDGOQFOQNFH-UHFFFAOYSA-N
Isomeric SMILESNCC(O)=O
Average Molecular Weight75.0666
Monoisotopic Molecular Weight75.032028409
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 32.00%; H 6.71%; N 18.66%; O 42.63%DFC
Melting PointMp 292 (262°)° dec.DFC
Boiling PointNot Available
Experimental Water Solubility249 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.21HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.78 (25°)DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-2900000000-0ef96bcf06ce475afcddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dj-1900000000-1d289099ac79cfb8bb19View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-7910000000-6c972a683dfb75b69331View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-0900000000-ef69e38ee6cebc2ece00View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2910000000-3215b9e40f20c7b306cdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-719b7f248956f13a312dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0900000000-99b4fc43740b21edc786View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1910000000-4cff4d14c73acff9442fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-2900000000-0ef96bcf06ce475afcddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1900000000-1d289099ac79cfb8bb19View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0002-4960000000-2c6fa028e985c6019854View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-7910000000-6c972a683dfb75b69331View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2910000000-3215b9e40f20c7b306cdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0900000000-ef69e38ee6cebc2ece00View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ds-2900000000-ffffed9c78c16a884e4aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004r-3900000000-f288b50b7b6890429811View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1900000000-c76140c31c1f120e4b9dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-f0a2cfbefb9fcd9b6c3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-b8bbfc1276d5adb1ba04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-6001578fc511ba3fefefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-79b2a0a9d93de6a62358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-9290dbe208c4744f4431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-6001578fc511ba3fefefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-79b2a0a9d93de6a62358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9290dbe208c4744f4431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-9000000000-605b44ac311a9af4bb7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-9000000000-725357e461c898a7451eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-9f3930e66b117ad91dcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-b3336097dddbb5e22871View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-9000000000-719b7f248956f13a312dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-9000000000-342ab462db0835abb3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0ar1-9010000000-9daadc1d169a8530926dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-07y0-9220000000-8c7785f1f3aa8052679fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0ula-9110000000-43ada06fe1b56b4e9fccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-017i-9000000000-fbd78fbb48f082235f42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-004i-9000000000-c38d0fb28793438083a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Positivesplash10-004i-9000000000-18a7ae48c7b0e15cdf18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-342ab462db0835abb3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ar1-9010000000-9daadc1d169a8530926dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-07y0-9220000000-8c7785f1f3aa8052679fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ula-9110000000-43ada06fe1b56b4e9fccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-017i-9000000000-fbd78fbb48f082235f42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-89b2c043a5afe3ebc6f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-b4046e208ee8adb87021View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-222d6c3a1ba6afcd7ea9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID730
ChEMBL IDCHEMBL773
KEGG Compound IDC00037
Pubchem Compound ID750
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID1062
DrugBank IDDB00145
HMDB IDHMDB00123
CRC / DFC (Dictionary of Food Compounds) IDBCV25-I:BCV25-I
EAFUS ID1527
Dr. Duke IDGLYCINE|GYLCINE
BIGG ID33610
KNApSAcK IDC00001361
HET IDGLY
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1008481
SuperScent IDNot Available
Wikipedia IDGlycine
Phenol-Explorer Metabolite ID1062
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti acidDUKE
anti aldosteronic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gastriticDUKE
anti prostatiticDUKE
anti pruritic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti sicklingDUKE
anti ulcer49201 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 preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
neuro inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
uricosuricDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.CHEBI
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.CHEBI
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrialGCATO75600
Trifunctional purine biosynthetic protein adenosine-3GARTP22102
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Glycine amidinotransferase, mitochondrialGATMP50440
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Glycine--tRNA ligaseGARSP41250
Aminomethyltransferase, mitochondrialAMTP48728
Glutathione synthetaseGSSP48637
Serine hydroxymethyltransferase, mitochondrialSHMT2P34897
Serine hydroxymethyltransferase, cytosolicSHMT1P34896
Glycine dehydrogenase [decarboxylating], mitochondrialGLDCP23378
Glycine cleavage system H protein, mitochondrialGCSHP23434
Vesicular inhibitory amino acid transporterSLC32A1Q9H598
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Serine hydroxymethyltransferaseDKFZp686P09201Q5HYG8
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Ammonia RecyclingSMP00009 map00910
Bile Acid BiosynthesisSMP00035 map00120
Carnitine SynthesisSMP00465 Not Available
Glutathione MetabolismSMP00015 map00480
Glycine and Serine MetabolismSMP00004 map00260
Methionine MetabolismSMP00033 map00270
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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.