| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-01-20 18:36:16 UTC |
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| NP-MRD ID | NP0000959 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Glycine |
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| Description | Glycine (Gly), is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Glycine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Glycine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid and is the simplest of all amino acids. In humans, glycine is a nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult human ingests 3 to 5 grams of glycine daily. Glycine is a colorless, sweet-tasting crystalline solid. It is the only achiral proteinogenic amino acid. Glycine was discovered in 1820 by the French chemist Henri Braconnot when he hydrolyzed gelatin by boiling it with sulfuric acid. The name comes from the Greek word glucus or "sweet tasting". Glycine is biosynthesized in the body from the amino acid serine, which is in turn derived from 3-phosphoglycerate. In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). In addition to being synthesized from serine, glycine can also be derived from threonine, choline or hydroxyproline via inter-organ metabolism of the liver and kidneys. Glycine is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine synthase pathway. In this context, the enzyme system involved glycine metabolism is called the glycine cleavage system. The glycine cleavage system catalyzes 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 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. Glycine is involved in the body's production of DNA, hemoglobin, and collagen, and in the release of energy. The principal function of glycine is as a precursor to proteins. Most proteins incorporate only small quantities of glycine, a notable exception being collagen, which contains about 35% glycine. In higher eukaryotes, delta-aminolevulinic acid, the key precursor to porphyrins (needed for hemoglobin and cytochromes), is biosynthesized from glycine and succinyl-CoA by the enzyme ALA synthase. Glycine provides the central C2N subunit of all purines, which are key constituents of DNA and RNA. 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). |
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| Structure | InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) |
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| Synonyms | | Value | Source |
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| 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 | | Glycine, monopotassium salt | MeSH | | Monopotassium salt glycine | MeSH | | Salt glycine, monopotassium | MeSH |
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| Chemical Formula | C2H5NO2 |
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| Average Mass | 75.0666 Da |
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| Monoisotopic Mass | 75.03203 Da |
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| IUPAC Name | 2-aminoacetic acid |
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| Traditional Name | glycine |
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| CAS Registry Number | 56-40-6 |
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| SMILES | NCC(O)=O |
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| InChI Identifier | InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) |
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| InChI Key | DHMQDGOQFOQNFH-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-07-25 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| 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). |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Alpha amino acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 262.2 °C | Not Available | | Boiling Point | 240.94 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | | Water Solubility | 249 mg/mL | Not Available | | LogP | -3.21 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
- Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [PubMed:6696735 ]
- Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
- Collins JW, Macdermott S, Bradbrook RA, Keeley FX Jr, Timoney AG: Is using ethanol-glycine irrigating fluid monitoring and 'good surgical practice' enough to prevent harmful absorption during transurethral resection of the prostate? BJU Int. 2006 Jun;97(6):1247-51. [PubMed:16686720 ]
- Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
- Christie GR, Ford D, Howard A, Clark MA, Hirst BH: Glycine supply to human enterocytes mediated by high-affinity basolateral GLYT1. Gastroenterology. 2001 Feb;120(2):439-48. [PubMed:11159884 ]
- Jones CM, Smith M, Henderson MJ: Reference data for cerebrospinal fluid and the utility of amino acid measurement for the diagnosis of inborn errors of metabolism. Ann Clin Biochem. 2006 Jan;43(Pt 1):63-6. [PubMed:16390611 ]
- Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
- Bennett FI, Jackson AA: Glycine is not formed through the amino transferase reaction in human or rat placenta. Placenta. 1998 May;19(4):329-31. [PubMed:9639330 ]
- Gomeza J, Ohno K, Hulsmann S, Armsen W, Eulenburg V, Richter DW, Laube B, Betz H: Deletion of the mouse glycine transporter 2 results in a hyperekplexia phenotype and postnatal lethality. Neuron. 2003 Nov 13;40(4):797-806. [PubMed:14622583 ]
- Boneh A, Degani Y, Harari M: Prognostic clues and outcome of early treatment of nonketotic hyperglycinemia. Pediatr Neurol. 1996 Sep;15(2):137-41. [PubMed:8888048 ]
- Dicke JM, Verges D, Kelley LK, Smith CH: Glycine uptake by microvillous and basal plasma membrane vesicles from term human placentae. Placenta. 1993 Jan-Feb;14(1):85-92. [PubMed:8456092 ]
- Prescot AP, de B Frederick B, Wang L, Brown J, Jensen JE, Kaufman MJ, Renshaw PF: In vivo detection of brain glycine with echo-time-averaged (1)H magnetic resonance spectroscopy at 4.0 T. Magn Reson Med. 2006 Mar;55(3):681-6. [PubMed:16453318 ]
- Byard RW, Harrison R, Wells R, Gilbert JD: Glycine toxicity and unexpected intra-operative death. J Forensic Sci. 2001 Sep;46(5):1244-6. [PubMed:11569574 ]
- Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. [PubMed:15780050 ]
- Van Hove JL, Vande Kerckhove K, Hennermann JB, Mahieu V, Declercq P, Mertens S, De Becker M, Kishnani PS, Jaeken J: Benzoate treatment and the glycine index in nonketotic hyperglycinaemia. J Inherit Metab Dis. 2005;28(5):651-63. [PubMed:16151895 ]
- Li K, Siefkes MJ, Li W: Cervidins A-D: Novel Glycine Conjugated Fatty Acids from the Tarsal Gland of Male Whitetail Deer, Odocoileus virginianus. J Chem Ecol. 2021 Mar;47(3):243-247. doi: 10.1007/s10886-021-01255-0. Epub 2021 Feb 24. [PubMed:33629151 ]
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