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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:59 UTC
Update Date2019-07-23 06:08:59 UTC
HMDB IDHMDB0031547
Secondary Accession Numbers
  • HMDB31547
Metabolite Identification
Common NameL-Cyclo(alanylglycyl)
DescriptionL-Cyclo(alanylglycyl), also known as alanylglycine anhydride or cyclo(ala-gly), belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Cyclo(alanylglycyl) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-Cyclo(alanylglycyl) has been detected, but not quantified in, cocoa and cocoa products. This could make L-cyclo(alanylglycyl) a potential biomarker for the consumption of these foods.
Structure
Data?1563862139
Synonyms
ValueSource
3-Methyl-2,5-dioxopiperazineChEBI
3-Methyl-2,5-piperazinedioneChEBI
Alanylglycine anhydrideChEBI
Cyclo(ala-gly)ChEBI
Cyclo(alanyl-glycyl)ChEBI
Cyclo(alanylglycyl)ChEBI
CycloglycylalanineChEBI
Glycylalanine anhydrideChEBI
3-Methyl-(S)-2,5-piperazinedioneHMDB
3-Methylpiperazine-2,5-dioneHMDB
L-3-Methyl-2,5-piperazinedioneHMDB
L-Alanylglycine anhydrideHMDB
L-Cyclo(alanyl-glycyl)HMDB
L-Glycylalanine anhydrideHMDB
L-MethyldiacipiperazineHMDB
Chemical FormulaC5H8N2O2
Average Molecular Weight128.1292
Monoisotopic Molecular Weight128.05857751
IUPAC Name3-methylpiperazine-2,5-dione
Traditional Name3-methylpiperazine-2,5-dione
CAS Registry Number4526-77-6
SMILES
CC1NC(=O)CNC1=O
InChI Identifier
InChI=1S/C5H8N2O2/c1-3-5(9)6-2-4(8)7-3/h3H,2H2,1H3,(H,6,9)(H,7,8)
InChI KeyICCHEGCKVBMSTF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • 1,4-diazinane
  • Piperazine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility250 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility22.1 g/LALOGPS
logP-1.6ALOGPS
logP-1.6ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)10.94ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.1 m³·mol⁻¹ChemAxon
Polarizability12.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053l-9000000000-a112f748d81443ef43d6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9100000000-235aec5f8d254471ac73Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053l-9000000000-a112f748d81443ef43d6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9100000000-235aec5f8d254471ac73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-81f0137991f4a9549c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-ef58841914083a2020e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5900000000-1248babcc12c1daf04b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-6990706ff3f54b112e91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-eb864f62f89c6f805038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-b9575017ddb5f3da293fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8b70a383bfb6a721df1bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008158
KNApSAcK IDNot Available
Chemspider ID96562
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107297
PDB IDNot Available
ChEBI ID144050
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .