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Glycine (FDB000484)

Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2020-09-17 15:42:09 UTC
Primary IDFDB000484
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycine
DescriptionGlycine, 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 Number56-40-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-222d6c3a1ba6afcd7ea92014-09-20View Spectrum
GC-MSGlycine, 3 TMS, GC-MS Spectrumsplash10-00dj-2900000000-0ef96bcf06ce475afcddSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00dj-1900000000-1d289099ac79cfb8bb19Spectrum
GC-MSGlycine, 3 TMS, GC-MS Spectrumsplash10-00di-7910000000-6c972a683dfb75b69331Spectrum
GC-MSGlycine, 2 TMS, GC-MS Spectrumsplash10-0udi-0900000000-ef69e38ee6cebc2ece00Spectrum
GC-MSGlycine, 3 TMS, GC-MS Spectrumsplash10-00di-2910000000-3215b9e40f20c7b306cdSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-719b7f248956f13a312dSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-99b4fc43740b21edc786Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00di-1910000000-4cff4d14c73acff9442fSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00dj-2900000000-0ef96bcf06ce475afcddSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00dj-1900000000-1d289099ac79cfb8bb19Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-0002-4960000000-2c6fa028e985c6019854Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00di-7910000000-6c972a683dfb75b69331Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00di-2910000000-3215b9e40f20c7b306cdSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-ef69e38ee6cebc2ece00Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-00ds-2900000000-ffffed9c78c16a884e4aSpectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-004r-3900000000-f288b50b7b6890429811Spectrum
GC-MSGlycine, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-c76140c31c1f120e4b9dSpectrum
Predicted GC-MSGlycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-f0a2cfbefb9fcd9b6c3eSpectrum
Predicted GC-MSGlycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9300000000-b8bbfc1276d5adb1ba04Spectrum
Predicted GC-MSGlycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-9000000000-725357e461c898a7451e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-9f3930e66b117ad91dca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-b3336097dddbb5e228712012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-9000000000-719b7f248956f13a312d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-6001578fc511ba3fefef2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-79b2a0a9d93de6a623582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-9290dbe208c4744f44312012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-9000000000-342ab462db0835abb3d22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0ar1-9010000000-9daadc1d169a8530926d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-07y0-9220000000-8c7785f1f3aa8052679f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0ula-9110000000-43ada06fe1b56b4e9fcc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-017i-9000000000-fbd78fbb48f082235f422012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-004i-9000000000-c38d0fb28793438083a92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Positivesplash10-004i-9000000000-18a7ae48c7b0e15cdf182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-6001578fc511ba3fefef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-79b2a0a9d93de6a623582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9290dbe208c4744f44312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-9000000000-605b44ac311a9af4bb7a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-342ab462db0835abb3d22017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-9000000000-c6b1ebc1dba89b6a61842015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-851aa6a0263541a8b2492015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-d3b5624412082bb2cf602015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-89b2c043a5afe3ebc6f62015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-b4046e208ee8adb870212015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-36521e440c602bd2ca5a2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.5 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H 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
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.