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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-03-03 10:25:52 UTC
Update Date2020-02-26 21:35:45 UTC
HMDB IDHMDB0011733
Secondary Accession Numbers
  • HMDB11733
Metabolite Identification
Common NameGlycyl-glycine
DescriptionThe simplest peptide, made of two glycine molecules; used in the synthesis of more complicated peptides. 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 ).
Structure
Data?1582752945
Synonyms
ValueSource
2-(Aminoacetamido)acetic acidChEBI
[(Aminoacetyl)amino]acetic acidChEBI
Gly-glyChEBI
Gly2ChEBI
Glycine dipeptideChEBI
N-GlycylglycineChEBI
2-(Aminoacetamido)acetateGenerator
[(Aminoacetyl)amino]acetateGenerator
((Aminoacetyl)amino)acetic acidHMDB
alpha-GlycylglycineHMDB
DiglycineHMDB
N-GLYCYL- glycineHMDB
Glycylglycine hydrochlorideHMDB
Glycyl glycineHMDB
Glycylglycine monohydrochlorideHMDB
Hydrochloride, glycylglycineHMDB
Monohydrochloride, glycylglycineHMDB
N GlycylglycineHMDB
Glycyl-glycineMeSH
Chemical FormulaC4H8N2O3
Average Molecular Weight132.1179
Monoisotopic Molecular Weight132.053492132
IUPAC Name2-(2-aminoacetamido)acetic acid
Traditional NameGly-Gly
CAS Registry Number556-50-3
SMILES
NCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C4H8N2O3/c5-1-3(7)6-2-4(8)9/h1-2,5H2,(H,6,7)(H,8,9)
InChI KeyYMAWOPBAYDPSLA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility166 mg/mL at 21 °CNot Available
LogP-2.92HANSCH,C ET AL. (1995)
Predicted Molecular Properties
PropertyValueSource
Water Solubility82.1 g/LALOGPS
logP-3.2ALOGPS
logP-4.5ChemAxon
logS-0.21ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.81 m³·mol⁻¹ChemAxon
Polarizability12.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available128.09631661259
DarkChem[M-H]-PredictedNot Available121.68431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Glycyl-glycine,1TMS,#11535.6143https://arxiv.org/abs/1905.12712
Glycyl-glycine,1TMS,#21573.317https://arxiv.org/abs/1905.12712
Glycyl-glycine,1TMS,#31531.1324https://arxiv.org/abs/1905.12712
Glycyl-glycine,1TBDMS,#11767.7527https://arxiv.org/abs/1905.12712
Glycyl-glycine,1TBDMS,#21833.5206https://arxiv.org/abs/1905.12712
Glycyl-glycine,1TBDMS,#31752.4114https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-2910000000-ba948ec1f3049dba68902014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-91132b8ff819b3ae47dc2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-e81c9e2483d01587c1bd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-156d6e678bff48157df22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-4cc7d622d8302ea789982017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1910000000-4b3d1fa3d216c551cb122017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-588aa5f9b282e25fb0052017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-de41939f179394ca4fd92017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-6a5f2500f08c12371f1f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2910000000-ba948ec1f3049dba68902017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-91132b8ff819b3ae47dc2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-8abf1a0641d024ca83102017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05a9-9100000000-7a4991aa2e80bb0b67092017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-ed69bb1a3dbb10d0d5e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-9100000000-d1fb7ab0c1ba8cc658352017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-7ba83a3b96d2fc869ebe2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-6173af951359b504bcd82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-939e8bb535cf951463462017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-008i-9800000000-bda55e81f5401b1bf95f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-6900000000-086c493e2bef9931c65e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-6446e10ba29e02e8889d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-414da3e4ba078845db832017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-838fb02e1a4a51356aac2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01b9-9000000000-2dce65916bdcc5799b7b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-7bab12a20740403750892017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-60572175e58a269c21cb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5b0b47aadbc64a0c08932021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-6dbb65e50eeae6f5b11c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-52dc384d9194cbfb6b462021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05g0-9100000000-0294e692c3988bae4d9b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-05g0-9000000000-a23bc0b136ea4bdb90d82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-3b2fa1da47acfdc57b652021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9500000000-5bb432a63f09472025a82016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00gi-9000000000-985944270c18616f5da32016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05e9-9000000000-4ad263a0b78114d654fd2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-c1e049bc22bd20fc2b122016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-9500000000-1039b99bd3cc506dcfdb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-1cf10876a736a8090b012016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SweatDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specifiedscreen-positive CF details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. 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 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028413
KNApSAcK IDNot Available
Chemspider ID10690
KEGG Compound IDC02037
BioCyc IDGLYCYLGLYCINE
BiGG IDNot Available
Wikipedia LinkGlycylglycine
METLIN IDNot Available
PubChem Compound11163
PDB IDNot Available
ChEBI ID17201
Food Biomarker OntologyNot Available
VMH IDGLYGLY
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]