You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2009-03-03 10:25:52 UTC
Update Date2017-09-25 11:35:16 UTC
HMDB IDHMDB0011733
Secondary Accession Numbers
  • HMDB11733
StatusDetected and Quantified
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
Thumb
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 hydrochlorideMeSH
Glycyl glycineMeSH
Glycylglycine monohydrochlorideMeSH
Hydrochloride, glycylglycineMeSH
Monohydrochloride, glycylglycineMeSH
N GlycylglycineMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Physiological effect
Health effect:
Health condition:
Cancer:
Physical Properties
StateSolid
Experimental 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 Properties
PropertyValueSource
Water Solubility82.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.81 m3·mol-1ChemAxon
Polarizability12.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-2910000000-ba948ec1f3049dba6890View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-91132b8ff819b3ae47dcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-e81c9e2483d01587c1bdView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-156d6e678bff48157df2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-4cc7d622d8302ea78998View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1910000000-4b3d1fa3d216c551cb12View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1900000000-588aa5f9b282e25fb005View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9700000000-de41939f179394ca4fd9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9800000000-6a5f2500f08c12371f1fView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2910000000-ba948ec1f3049dba6890View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2900000000-91132b8ff819b3ae47dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-ed69bb1a3dbb10d0d5e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-9100000000-d1fb7ab0c1ba8cc65835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-7ba83a3b96d2fc869ebeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-6173af951359b504bcd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-939e8bb535cf95146346View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-008i-9800000000-bda55e81f5401b1bf95fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-6900000000-086c493e2bef9931c65eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-6446e10ba29e02e8889dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-414da3e4ba078845db83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-838fb02e1a4a51356aacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01b9-9000000000-2dce65916bdcc5799b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-7bab12a2074040375089View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    UrineDetected but not Quantified Not AvailableNot AvailableNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
    Prostate Cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    SweatDetected but not Quantified Infant (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 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB028413
    KNApSAcK IDNot Available
    Chemspider ID10690
    KEGG Compound IDC02037
    BioCyc IDDIOXOPIPERAZINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0011733
    METLIN IDNot Available
    PubChem Compound11163
    PDB IDNot Available
    ChEBI ID17201
    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 ]