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Showing metabocard for Glycine (BMDB0000123)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:50 UTC
Update Date2020-06-04 21:57:34 UTC
MCDB ID BMDB0000123
Secondary Accession Numbers
  • BMDB00123
Metabolite Identification
Common NameGlycine
DescriptionGlycine, also known as Gly or aminoessigsaeure, 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glycine exists in all living species, ranging from bacteria to humans. Glycine is a potentially toxic compound. Glycine has been found to be associated with several diseases known as crohn's disease, leukemia, phosphoserine aminotransferase deficiency, and hyperglycinemia, lactic acidosis, and seizures; also glycine has been linked to the inborn metabolic disorders including n-acetylglutamate synthetase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC2H5NO2
Average Molecular Weight75.0666
Monoisotopic Molecular Weight75.032028409
IUPAC Name2-aminoacetic acid
Traditional Nameglycine
CAS Registry Number56-40-6
SMILES
NCC(O)=O
InChI Identifier
InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
InChI KeyDHMQDGOQFOQNFH-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).
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point262.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility249 mg/mLNot Available
LogP-3.21HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified33 - 1100 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected and Quantified163 - 855 uM details
Detected and Quantified33 - 1109 uM details
Detected and Quantified9591 uM details
Detected and Quantified9591 uM details
Detected and Quantified9458 uM details
Detected and Quantified9458 uM details
Detected and Quantified9325 uM details
Detected and Quantified9325 uM details
Detected and Quantified9325 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified68 +/- 3 uM details
Detected and Quantified77 +/- 3 uM details
Detected and Quantified65 +/- 3 uM details
Detected and Quantified72 +/- 2 uM details
HMDB IDHMDB0000123
DrugBank IDDB00145
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000484
KNApSAcK IDC00001361
Chemspider ID730
KEGG Compound IDC00037
BioCyc IDGLY
BiGG ID33610
Wikipedia LinkGlycine
METLIN ID20
PubChem Compound750
PDB IDNot Available
ChEBI ID15428
References
Synthesis ReferenceAnslow, Winston K.; King, Harold. Synthesis of glycine. Journal of the Chemical Society (1929), 2163-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  4. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  5. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]